Methanol → 4-Chloro-2-(trifluoromethyl)phenylacetic acid methyl ester

HRID 406363Notes

Reaction equation

HRID 406363 reaction equation
S(Cl)(Cl)=O.[Cl:5][C:6]1[CH:11]=[CH:10][C:9]([CH2:12][C:13]([OH:15])=[O:14])=[C:8]([C:16]([F:19])([F:18])[F:17])[CH:7]=1.[CH3:20]O>>[Cl:5][C:6]1[CH:11]=[CH:10][C:9]([CH2:12][C:13]([O:15][CH3:20])=[O:14])=[C:8]([C:16]([F:17])([F:18])[F:19])[CH:7]=1

Participants

4

Reactant 3

HCID 887MethanolHCID 24386Thionyl ChlorideHCID 32777474-Chloro-2-(trifluoromethyl)phenylacetic acid

Product 1

HCID 861160344-Chloro-2-(trifluoromethyl)phenylacetic acid methyl ester

Procedure

Thionyl chloride (9.5 mL) was added dropwise to a solution of 4-chloro-2-(trifluoromethyl)phenylacetic acid (CAS #601513-31-9, 10.5 g) in methanol (50 mL) under ice-cooling. Then, the reaction solution was heated under reflux for three hours. The reaction solution was concentrated under reduced pressure. A saturated sodium bicarbonate solution and ethyl acetate were added to the resulting residue, and the organic layer was separated. The resulting organic layer was sequentially washed with a saturated sodium bicarbonate solution and brine, dried over anhydrous magnesium sulfate and then concentrated under reduced pressure to obtain 10.96 g of the title compound. 1H-NMR (CDCl3) δ (ppm): 3.71 (s, 3H), 3.80 (s, 2H), 7.35 (d, J=8.4 Hz, 1H), 7.50 (dd, J=8.4, 2.0 Hz, 1H), 7.65 (d, J=2.0 Hz, 1H).

Workup

  1. temperaturecooling
  2. temperatureThen, the reaction solution was heated
  3. temperatureunder reflux for three hours
  4. concentrationThe reaction solution was concentrated under reduced pressure
  5. additionA saturated sodium bicarbonate solution and ethyl acetate were added to the resulting residue
  6. customthe organic layer was separated
  7. washThe resulting organic layer was sequentially washed with a saturated sodium bicarbonate solution and brine
  8. dry with materialdried over anhydrous magnesium sulfate
  9. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-3197d77ab77c4b518fd031f1cada8c9c
Source dataset
uspto-grants-2014_06
Patent number
US08754100B2

Reaction notes

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