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Chemical Structure| 89894-44-0 Chemical Structure| 89894-44-0

Structure of 89894-44-0

Chemical Structure| 89894-44-0

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CAS No.: 89894-44-0

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Product Details of [ 89894-44-0 ]

CAS No. :89894-44-0
Formula : C8H6Cl2O
M.W : 189.04
SMILES Code : O=C(Cl)C1=C(C)C=CC=C1Cl
MDL No. :MFCD12025218
InChI Key :NPRWNQSMJBAKCL-UHFFFAOYSA-N
Pubchem ID :22382040

Safety of [ 89894-44-0 ]

GHS Pictogram:
Signal Word:Danger
Hazard Statements:H314
Precautionary Statements:P280-P305+P351+P338
Class:8
UN#:3265
Packing Group:Ⅲ

Application In Synthesis of [ 89894-44-0 ]

* 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.

  • Upstream synthesis route of [ 89894-44-0 ]
  • Downstream synthetic route of [ 89894-44-0 ]

[ 89894-44-0 ] Synthesis Path-Upstream   1~1

  • 1
  • [ 67-56-1 ]
  • [ 89894-44-0 ]
  • [ 99585-14-5 ]
YieldReaction ConditionsOperation in experiment
87%
Stage #1: at 0℃; for 0.75 h;
Stage #2: at 20℃; 		A. A suspension of 2-chloro-6-methyl-benzoic acid (7.82 g, 45.8 MMOL) in thionyl chloride (20.0 mL, 275 MMOL), was immersed in an oil bath held at 85°C, and refluxed for 16 hours. The resulting pale brown solution was concentrated under reduced pressure to afford the acid chloride as a pale brown oil. This material was carried on to the ester formation without purification. The acid chloride (45.8 mmol from previous step) was dissolved in DICHLOROMETHANE (20 mL) and the mixture cooled in an ice bath. Methanol (10 mL, 247 MMOL) was added and the ice bath was then removed. HPLC of the reaction mixture 45 minutes after removal of the ice bath showed a 4: 1 mixture of starting acid: product ester. The reaction mixture was then treated with triethylamine (15 mL, 108 MMOL) dropwise over several minutes. The triethylamine addition was exothermic and led to the production of a lot of smoke in the reaction flask. After stirring overnight at ambient temperature HPLC indicated complete conversion to product. The reaction mixture was poured into a mixture of ether (200 mL) and saturated aqueous sodium hydrogen carbonate solution (100 mL). The layers were separated and the basic aqueous layer was extracted with ether (3 x 50 mL). The organic layers were combined and washed with brine, then dried (NA2SO4), filtered, and concentrated under reduced pressure to afford a yellow oil. The material was purified by flash chromatography eluting with a gradient from 0percent to 10percent ethyl acetate/hexane to afford 2-chloro-6-methylbenzoic acid methyl ester (7.38 g, 87percent yield) as a clear colorless liquid :'H-NMR (400 MHz, CDCI3) : 8 7.24-7. 19 (2H, m), 7.14-7. 08 (1H, m), 3.95 (3H, s), 2.32 (3H, s) ppm.
72% at 20℃; for 3 h; Preparation XVII: 2-chloro-6-dimethylaminomethyl-benzoic acid. Step 1. Synthesis of 2-bromomethyl-6-chloro-benzoic acid methyl ester.2-Chloro-6-methyl benzoic acid (5.8 g, 34.0 mmoles) was suspended in dichloromethane (100 ml). To the suspension was added DMF (250 mg, 3.4 mmoles) and then dropwise oxalyl chloride (3.9 ml, 44.2 mmoles). The resultant solution was stirred at ambient temperature for 24 hours. Further DMF (250 mg, 3.4 EPO <DP n="151"/>mmoles) and oxalyl chloride (3.9ml, 44.2 mmoles) was added to the reaction mixture, and the resultant solution stirred for a further 24 hours at ambient temperature. The reaction mixture was concentrated in vacuo. The residue was dissolved in methanol (100 ml) and stirred at ambient temperature for 3 hours. The reaction mixture was concentrated in vacuo. The residue was partitioned between ethyl acetate and sodium hydroxide solution (2N). The organic portion was washed with sodium hydroxide solution (2N), and then brine, dried (MgSO4), filtered and the concentrated in vacuo. The residue was purified by flash chromatography (eluent 3:5 EtOAc iPetrol to give 2-chloro-6-methyl-benzoic acid methyl ester as a yellow oil (4.5g, 72percent).
References: [1] Patent: WO2004/58717, 2004, A1, . Location in patent: Page 76.
[2] Patent: WO2006/77414, 2006, A1, . Location in patent: Page/Page column 149-150.
 

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