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3-(3-bromo-2-fluorophenyl)propanoyl chloride[ No CAS ]
[ 127425-74-5 ]
Yield
Reaction Conditions
Operation in experiment
86%
With aluminum (III) chloride; In dichloromethane; at 0 - 20℃; for 3.33333h;
To the solution of intermediate AF U3-BROMO-2-FLUOROPHENYL) acetic acid] (150 mg, 0. 61 MMOL) in CH2CI2 (10 mL) was added thionyl chloride (0. 13 mL, 1. 82 MMOL) and 2 drops of DMF. The mixture was stirred at rt overnight and concentrated down. The residue was dissolved in CH2CI2 (5 mL) and then added to a cold solution of AICI3 in CH2CI2 (5 mL). The reaction mixture was stirred at 0C for 20 min and then at rt for 3 h, poured into ice water and the mixture was extracted with CH2CI2. The organic layer was washed with saturated NAHC03, brine, dried over NA2SO4, filtered and concentrated down. Chromatography using a Biotage cartridge (25S) with the EtOAc/Hexane (10/90) afforded 5-bromo-4-fluoroindan- 1-one (120 mg, 86%). GC/MS [Exact Mass] 228 ;'H-NMR (DMSO-d6) 8 7. 74 (m, 1H), 7. 40 (d, 1H), 3. 12 (t, 2H), 2. 68 (m, 2H).
With aluminum (III) chloride; In dichloromethane; for 1.5h;Reflux;
A solution of crude 3-(3-bromo-2-fluorophenyl)propanoyl chloride (hg, 41.4 mmol) in dichloromethane (150 ml) was added dropwise to a refluxing suspension of A1C13 (8.29 g, 62.1 mmol) in dichloromethane (200 ml). The mixture was refluxed for 1.5 hours, poured into ice/concentrated hydrochloric acid and extracted with dichloromethane. The organic layers werecombined and concentrated under reduced pressure. The residue was purified by silica gel column chromatography to afford the title compound.
1-[(1S)-4'-{2-[(2S,5S)-2-(3,4-difluorophenyl)-5-methylpyrrolidin-1-yl]-2-oxoethyl}-4-fluoro-3',5'-dioxo-2,3-dihydrospiro[indene-1,2'-[1,4]oxazolidin]-5-yl]-3-methylurea[ No CAS ]
1-((S)-4-fluoro-3'-(2-((2S,5S)-2-methyl-5-(3,4,5-trifluorophenyl)pyrrolidin-1-yl)-2-oxoethyl)-2',4'-dioxo-2,3-dihydrospiro[indene-1,5'-oxazolidine]-5-yl)-3-methylurea[ No CAS ]
1-((R)-3'-(2-((2S,5S)-2-(3,4-difluorophenyl)-5-methylpyrrolidin-1-yl)-2-oxoethyl)-4-fluoro-2',4'-dioxo-2,3-dihydrospiro[indene-1,5'-oxazolidine]-5-yl)-3-methylurea[ No CAS ]
1-[(R)-4-fluoro-4'-{2-[(2S,5S)-2-methyl-5-(3,4,5-trifluorophenyl)pyrrolidin-1-yl]-2-oxoethyl}-3',5'-dioxo-2,3-dihydrospiro[indene-1,2'-[1,4]oxazolidin]-5-yl]-3-methylurea[ No CAS ]
5-bromo-4-fluoro-1-((trimethylsilyl)oxy)-2,3-dihydro-1H-indene-1-carbonitrile[ No CAS ]
Yield
Reaction Conditions
Operation in experiment
65%
With aluminum (III) chloride; In dichloromethane; at 20℃; for 5.0h;
Add aluminum trichloride (1.26g, 9.4mmol), <strong>[127425-74-5]5-bromo-4-fluoro-2,3-dihydro-1H-inden-1-one</strong> (10.7 g, 47mmol), dry dichloromethane (100mL) into a 100mL reaction flask, and slowly add dropwise under ice bath Trimethylsilyl cyanide (9.4g, 94mmol) was added and stirred at room temperature for 5 hours. The reaction solution was poured into saturated potassium hydrogen carbonate aqueous solution (200 mL), extracted with dichloromethane three times, and the organic phases were combined, dried over anhydrous sodium sulfate, and concentrated. After column chromatography, a white intermediate Int 381-1 (10 g) was obtained with a yield of 65%.
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