Methanol → Methyl 3-bromo-5-(trifluoromethyl)benzoate

HRID 1640145Notes

Reaction equation

HRID 1640145 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([CH:8]=[C:9]([C:11]([F:14])([F:13])[F:12])[CH:10]=1)[C:5]([OH:7])=[O:6].OS(O)(=O)=O.[CH3:20]O>>[Br:1][C:2]1[CH:3]=[C:4]([CH:8]=[C:9]([C:11]([F:12])([F:13])[F:14])[CH:10]=1)[C:5]([O:7][CH3:20])=[O:6]

Participants

4

Reactant 3

HCID 887MethanolHCID 1118Sulfuric AcidHCID 110867883-Bromo-5-(trifluoromethyl)benzoic acid

Product 1

HCID 18942156Methyl 3-bromo-5-(trifluoromethyl)benzoateYield 92%

Procedure

To a solution of 3-bromo-5-(trifluoromethyl)benzoic acid (12.43 g, 0.04620 mol) in MeOH (200 mL) was added H2SO4 (8 mL). The reaction mixture was heated at reflux overnight and then concentrated to small volume. The residue was extracted with EtOAc and washed with water, brine, aq. sat. NaHCO3, and brine. The organic solution was concentrated to give methyl 3-bromo-5-(trifluoromethyl)benzoate (12.7 g, 92%). 1H NMR (300 MHz, CDCl3) δ: 8.36 (s, 1H), 8.23 (s, 1H), 7.95 (s, 1H), and 3.97 (s, 3H).

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureat reflux overnight
  3. concentrationconcentrated to small volume
  4. extractionThe residue was extracted with EtOAc
  5. washwashed with water, brine, aq. sat. NaHCO3, and brine
  6. concentrationThe organic solution was concentrated

Sources & evidence

ORD record
ord-148c8a5e73ef4d50b8578450b8d49838
Source dataset
uspto-grants-2012_02
Patent number
US08110687B2

Reaction notes

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