Reaction #2139948

ord-25325fd3fced4b368c14c404884dc5fc

Reaction equation

CCCCC[C@H]1CC[C@H](c2ccc(Br)c(C(=O)O)c2F)CC1
trans-6-bromo-2-fluoro-3-(4-pentylcyclohexyl)-benzoic acid
O=C([O-])[O-].[K+].[K+]
potassium carbonate
CI
methyl iodide
→
CCCCCC1CCC(c2ccc(Br)c(C(=O)OC)c2F)CC1
methyl 6-bromo-2-fluoro-3-(4-pentylcyclohexyl)benzoate
Yield 101.6%

Reactants

CCCCC[C@H]1CC[C@H](c2ccc(Br)c(C(=O)O)c2F)CC1
trans-6-bromo-2-fluoro-3-(4-pentylcyclohexyl)-benzoic acid
O=C([O-])[O-].[K+].[K+]
potassium carbonate
CI
methyl iodide

Reagents

None

Solvents

CC(C)=O
acetone

Conditions

Detailed conditions
See reaction.notes.procedure_details.

Workup

  1. 1
    Temperaturethe mixture was refluxed overnight
  2. 2
    FiltrationThe batch was filtered
  3. 3
    workup.DISTILLATIONthe solvent was distilled off

Procedure

17.1 g (46.0 mmol) of trans-6-bromo-2-fluoro-3-(4-pentylcyclohexyl)-benzoic acid were dissolved in 70 ml of acetone, 7.66 g (55.4 mmol) of potassium carbonate and 3.14 ml (50.6 mmol) of methyl iodide were added, and the mixture was refluxed overnight. The batch was filtered, and the solvent was distilled off, giving 18 g (100%) of methyl 6-bromo-2-fluoro-3-(4-pentylcyclohexyl)benzoate as a colourless oil, which was reacted further without further purification.

Source

DOI: 10.6084/m9.figshare.5104873.v1Patent: US07326447B2uspto-grants-2008_02