Hydrochloric Acid → Methyl 4-(difluoromethyl)benzoate

HRID 1672566Notes

Reaction equation

HRID 1672566 reaction equation
[F:1][CH:2]([F:12])[C:3]1[CH:11]=[CH:10][C:6]([C:7]([OH:9])=[O:8])=[CH:5][CH:4]=1.Cl.[CH3:14]O>>[F:1][CH:2]([F:12])[C:3]1[CH:4]=[CH:5][C:6]([C:7]([O:9][CH3:14])=[O:8])=[CH:10][CH:11]=1

Participants

4

Reactant 3

HCID 313Hydrochloric AcidHCID 887MethanolHCID 207393254-(Difluoromethyl)benzoic acid

Product 1

HCID 22262108Methyl 4-(difluoromethyl)benzoate

Procedure

A solution of 4-(difluoromethyl)benzoic acid (5.47 g, 31.8 mmol) in MeOH (100 mL) was treated with concentrated aq HCl (0.5 mL, 6.0 mmol), and the reaction mixture was heated to reflux. After 24 hr the solution was cooled to ambient temperature and concentrated in vacuo. The residue was taken up in Et2O and washed with saturated aqueous NaHCO3 solution and brine, dried over MgSO4, filtered, and concentrated in vacuo. The result was 5.82 g (98%) of the title compound as a white solid. 1H NMR (300 MHz, DMSO-d6) δ 8.13-8.06 (m, 2H), 7.76-7.69 (m, 2H), 7.14 (t, J=55.5, 1H), 3.89 (s, 3H).

Workup

  1. temperaturethe reaction mixture was heated to reflux
  2. concentrationconcentrated in vacuo
  3. washwashed with saturated aqueous NaHCO3 solution and brine
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-f4e007f64d02451d81371448e3a45608
Source dataset
uspto-grants-2011_08
Patent number
US07998993B2

Reaction notes

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