* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.
With hydrogen bromide; Selectfluor In water at 20℃; for 1 h;
General procedure: 1a as example: To a stirred suspension of N-(p-tolyl)acetamide 1a (75 mg, 0.5 mmol) and Selectfluor (213 mg, 0.6 mmol) in water (3.0 mL) was added HBr (40percent aqueous, 0.08 mL, 0.55 mmol), and the mixture was stirred for 5 min at room temperature. After 1a was consumed, as indicated by TLC, the reaction mixture was quenched with saturated aqueous Na2S2O3 (2.0 mL) and water (20.0 mL), and extracted with CH2Cl2 (10.0 mL) three times. The residue obtained after evaporation of the solvent was purified by column chromatography on silica gel (petroleum ether–ethyl acetate = 6:1, v/v) to afford N-(2-bromo-4-methylphenyl)acetamide 2a as a white solid (108 mg, 95percent yield).
Reference：
[1] Chemistry - A European Journal, 2017, vol. 23, # 5, p. 1044 - 1047
[2] Tetrahedron Letters, 2016, vol. 57, # 48, p. 5390 - 5394
[3] Journal of Chemical Research, Synopses, 1997, # 11, p. 432 - 433
[4] European Journal of Organic Chemistry, 2018, vol. 2018, # 43, p. 5972 - 5979
[5] Gazzetta Chimica Italiana, 1908, vol. 38 II, p. 22
2
[ 38762-41-3 ]
[ 75-36-5 ]
[ 3460-23-9 ]
Yield
Reaction Conditions
Operation in experiment
92%
Stage #1: With triethylamine In dichloromethane at 20℃; for 0.0833333 h; Stage #2: at 0 - 20℃; for 2 h;
Compound α (1 g, 4.8 mmol) was dissolved in 10 mL of anhydrous methylene chloride. To this mixture was added triethylamine (0.68 mL, 4.8 mmol) and the reaction was stirred at room temperature for 5 min. Acetyl chloride (0.5 mL, 7.2 mmol) was then added at 0 0C and the mixture stirred at room temperature for 2 hours. Water and dichloromethane were added and the layers separated. The organic layer was then dried over sodium sulfate and concentrated to give 1.11 g, 92percent yield of compound b. To a solution of b (500 mg, 2.01 mmol), cyclopropyl boronic acid (225 mg, 2.62 mmol), potassium phosphate (1.49 g, 7.04 mmol) and tricyclohexylphosphine (56 mg, 0.2 mmol) in toluene (10 mL) and water (0.4 mL) under nitrogen atmosphere was added palladium acetate (23 mg, 0.1 mmol). T he mixture was heated to 100 0C for 3h and then cooled to room temperature. Water was added and the mixture extracted with ethyl acetate, dried over sodium sulfate and concentrated to give 550mg of crude product c that was used in the next step without further purification. Compound c (500mg, 2.4 mmol) was dissolved in 4 mL of ethanol. Aqueous IN HCl (4 mL) was added and the mixture stirred at reflux for 8 hours. The solvent was removed in vacuo to afford 440mg of compound d which was used in the next step without further purification. Compound d (440mg, 2.6 mmol) was dissolved in 14 mL of dichloromethane. Sodium bicarbonate (7 mL, sat. solution) and thiophosgene (0.2 mL, 2.6 mmol) were added and the mixture stirred at room temperature for Ih. Then, the organic layer was separated, dried over sodium sulfate and concentrated to afford 877 mg, 99percent yield of compound e which was used in the next step without further purification Compound e (447mg, 2.1 mmol) was dissolved in 3 mL of dimethylformamide, aminoguanidine hydrochloride salt (355 mg, 3.2 mmol) and diisopropyl ethylamine (0.56 mL, 3.2 mmol) were added and the mixture stirred at 50 0C for 18 hours. The mixture was then concentrated and to the resulting residue was added 2M aqueous sodium hydroxide solution (10 mL). The mixture was stirred at 50 0C for 18 hours and then cooled to room temperature. The resulting mixture was then neutralized with aqueous IN HCl and the precipitate (product) collected to give compound/ (240 mg, 44percent yield) Compounds/(89mg, 0.33 mmol) and g (94mg, 0.33 mmol) were dissolved in DMF (1.5 mL) and potassium carbonate (51mg, 0.37 mmol) was added. The mixture was stirred at room temperature for 18 hours. Water was then added to the mixture and the precipitate formed collected and purified by prep. TLC (90percent dichloromethane/ 10percent methanol) to give 116 mg, 68percent yield of compound h. Dichloroacetic acid (0.04 mL, 0.46 mmol) was added to a mixture of compound h (116mg, 0.23 mmol), benzyltriethyl ammonium bromide (183mg, 0.68 mmol) and sodium nitrite (304mg, 4.6 mmol) in dibromomethane (5 mL). The mixture was stirred at room temperature for 18 hours in the dark. The reaction mixture was then concentrated and the resulting residue was purified by prep. TLC (95percent dichloromethane /5percent methanol) to afford 99.10 mg of the sulfonic acid and 17.90 mg of title compound i.
Reference：
[1] Synthetic Communications, 2012, vol. 42, # 24, p. 3655 - 3663,9
[2] European Journal of Organic Chemistry, 2018, vol. 2018, # 34, p. 4748 - 4753
[3] Chemistry - A European Journal, 2017, vol. 23, # 29, p. 7031 - 7036
[4] Organic and Biomolecular Chemistry, 2018, vol. 16, # 30, p. 5433 - 5440
[5] Journal of the Indian Chemical Society, 1981, vol. 58, p. 447 - 453
[6] Journal of the Chemical Society, 1907, vol. 91, p. 1567
[7] Journal of the Chemical Society, 1916, vol. 109, p. 96
[8] Journal of the Chemical Society, 1923, vol. 123, p. 3394
4
[ 38762-41-3 ]
[ 108-24-7 ]
[ 3460-23-9 ]
Reference：
[1] Advanced Synthesis and Catalysis, 2007, vol. 349, # 14-15, p. 2286 - 2300
[2] Organic and Biomolecular Chemistry, 2018, vol. 16, # 21, p. 3881 - 3884
Reference：
[1] Journal of Chemical Research, Synopses, 1997, # 11, p. 432 - 433
7
[ 103-84-4 ]
[ 3460-23-9 ]
Reference：
[1] Organic and Biomolecular Chemistry, 2018, vol. 16, # 30, p. 5433 - 5440
[2] Organic and Biomolecular Chemistry, 2018, vol. 16, # 30, p. 5433 - 5440
[3] European Journal of Organic Chemistry, 2018, vol. 2018, # 34, p. 4748 - 4753
8
[ 106-40-1 ]
[ 3460-23-9 ]
Reference：
[1] Chemistry - A European Journal, 2017, vol. 23, # 29, p. 7031 - 7036
9
[ 38762-41-3 ]
[ 3460-23-9 ]
Reference：
[1] Journal of the Chemical Society, 1916, vol. 109, p. 96
10
[ 113117-16-1 ]
[ 3460-23-9 ]
Reference：
[1] Journal of the Chemical Society, 1916, vol. 109, p. 96
11
[ 99233-16-6 ]
[ 108-90-7 ]
[ 76-03-9 ]
[ 3460-23-9 ]
Reference：
[1] Journal of the Chemical Society, 1957, p. 2676,2678
[2] Journal of the Chemical Society, 1957, p. 2676,2678
[3] Journal of the Chemical Society, 1957, p. 2676,2678
12
[ 99233-16-6 ]
[ 64-19-7 ]
[ 3460-23-9 ]
Reference：
[1] Journal of the Chemical Society, 1902, vol. 81, p. 987
13
[ 114233-34-0 ]
[ 3460-23-9 ]
Reference：
[1] Journal of the Chemical Society, 1916, vol. 109, p. 96
[2] Journal of the Chemical Society, 1916, vol. 109, p. 96
14
[ 29551-82-4 ]
[ 64-19-7 ]
[ 3460-23-9 ]
Reference：
[1] Journal of the Chemical Society, 1901, vol. 79, p. 818
15
[ 533-17-5 ]
[ 10035-10-6 ]
[ 7697-37-2 ]
[ 3460-23-9 ]
Reference：
[1] Gazzetta Chimica Italiana, 1908, vol. 38 II, p. 22
16
[ 7647-01-0 ]
[ 103-88-8 ]
[ 127-65-1 ]
[ 3460-23-9 ]
Reference：
[1] Journal of the Chemical Society, 1923, vol. 123, p. 3394
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