Methanol → 5-Chloro-2-(trifluoromethyl)benzoic acid methyl ester

HRID 241437Notes

Reaction equation

HRID 241437 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([C:11]([F:14])([F:13])[F:12])=[C:6]([CH:10]=1)[C:7]([OH:9])=[O:8].S(Cl)(Cl)=O.[CH3:19]O>>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([C:11]([F:12])([F:13])[F:14])=[C:6]([CH:10]=1)[C:7]([O:9][CH3:19])=[O:8]

Participants

4

Reactant 3

HCID 887MethanolHCID 24386Thionyl ChlorideHCID 27738595-Chloro-2-(trifluoromethyl)benzoic acid

Product 1

HCID 463111105-Chloro-2-(trifluoromethyl)benzoic acid methyl esterYield 96.5%

Conditions

Temperature
70 °C

Procedure

Dissolve 5-chloro-2-(trifluoromethyl)benzoic acid (10 g, 0.044 mol) in MeOH (150 mL). Add thionyl chloride (50 g, 0.421 mol) slowly. Heat the resulting mixture to 70° C., and stir for 12 hours. Concentrate the mixture under reduced pressure. Pour the residue into water (100 mL), and extract the aqueous with EtOAc (2×200 mL). Dry the combined organics over sodium sulfate, and concentrate under reduced pressure to give the title compound (11.5 g, 96.5%) as an oil. 1H NMR (300 MHz, CDCl3,) δ 7.78 (d, J=2.1 Hz, 1H), 7.69 (d, J=8.4 Hz, 1H), 7.57 (dd, J=2.1, 8.7 Hz, 1H), 3.95 (s, 3H).

Workup

  1. concentrationConcentrate the mixture under reduced pressure
  2. additionPour the residue into water (100 mL)
  3. extractionextract the aqueous with EtOAc (2×200 mL)
  4. dry with materialDry the combined organics over sodium sulfate
  5. concentrationconcentrate under reduced pressure

Sources & evidence

ORD record
ord-b1985d3d8e414c7dbc7c4cf3b8f42d40
Source dataset
uspto-grants-2014_02
Patent number
US08648200B2

Reaction notes

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