Methyl iodide → HCID 58687479, compound

HRID 2052766Notes

Reaction equation

HRID 2052766 reaction equation
[Br:1][C:2]1[C:7]([C:8]([OH:10])=[O:9])=[C:6]([F:11])[C:5]([C@H:12]2[CH2:17][CH2:16][C@H:15]([CH2:18][CH2:19][CH2:20][CH2:21][CH3:22])[CH2:14][CH2:13]2)=[CH:4][CH:3]=1.[C:23](=O)([O-])[O-].[K+].[K+].CI>CC(C)=O>[Br:1][C:2]1[C:7]([C:8]([O:10][CH3:23])=[O:9])=[C:6]([F:11])[C:5]([CH:12]2[CH2:17][CH2:16][CH:15]([CH2:18][CH2:19][CH2:20][CH2:21][CH3:22])[CH2:14][CH2:13]2)=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 178444244HCID 178444244, compound

Product 1

HCID 58687479HCID 58687479, compoundYield 101.6%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

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.

Workup

  1. temperaturethe mixture was refluxed overnight
  2. filtrationThe batch was filtered
  3. distillationthe solvent was distilled off

Sources & evidence

ORD record
ord-25325fd3fced4b368c14c404884dc5fc
Source dataset
uspto-grants-2008_02
Patent number
US07326447B2

Reaction notes

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