Methanol → Methyl 4-bromo-3-fluorobenzoate

HRID 906064Notes

Reaction equation

HRID 906064 reaction equation
[Br:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([OH:8])=[O:7])=[CH:4][C:3]=1[F:11].S(=O)(=O)(O)O.[CH3:17]O>>[Br:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([O:8][CH3:17])=[O:7])=[CH:4][C:3]=1[F:11]

Participants

4

Reactant 3

HCID 887MethanolHCID 1118Sulfuric AcidHCID 27733414-Bromo-3-fluorobenzoic acid

Product 1

HCID 21951878Methyl 4-bromo-3-fluorobenzoateYield 97%

Conditions

Temperature
80 °C

Procedure

To 4-bromo-3-fluorobenzoic acid (2.00 g, 9.13 mmol) in methanol (12 ml) was added sulfuric acid (500 μl) and heated to 80° C. for 18 h then cooled to room temperature and concentrated. The residue was diluted with saturated sodium bicarbonate and extracted with ethyl acetate. The organic layer was dried over sodium sulfate, filtered, and then concentrated to afford (2.07 g, 97%) of methyl 4-bromo-3-fluorobenzoate, which was used without further purification. 1H NMR (400 MHz, CD3OD): 7.80-7.73 (m, 3H), 3.91 (s, 3H). MS (EI) for C8H6BrFO2: 234 (MH+).

Workup

  1. temperaturethen cooled to room temperature
  2. concentrationconcentrated
  3. additionThe residue was diluted with saturated sodium bicarbonate
  4. extractionextracted with ethyl acetate
  5. dry with materialThe organic layer was dried over sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-91b335b04d92423e9662bc5be52b14c6
Source dataset
uspto-grants-2011_09
Patent number
US08012956B2

Reaction notes

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