Lithium Hydroxide → 3,3-Difluorocyclohexanecarboxylic acid

HRID 750788Notes

Reaction equation

HRID 750788 reaction equation
[OH-].[Li+].[F:3][C:4]1([F:13])[CH2:9][CH:8]([C:10]([O-:12])=[O:11])[CH2:7][CH2:6][CH2:5]1>CO.C1COCC1.O>[F:3][C:4]1([F:13])[CH2:9][CH:8]([C:10]([OH:12])=[O:11])[CH2:7][CH2:6][CH2:5]1

Participants

6

Reactant 2

HCID 3939Lithium HydroxideHCID 86613679HCID 86613679, compound

Product 1

HCID 537528283,3-Difluorocyclohexanecarboxylic acid

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

A 2 M aqueous solution of lithium hydroxide (26 mL) was added to a solution of methyl (1R,2R)-2-2-bromophenyl)-5,5-difluorocyclohexanecarboxylate (1.81 g, 5.46 mmol) in a mixture of methanol (20 mL) and THF (10 mL) with rapid stirring at room temperature for 15 hours. The reaction mixture was then diluted with water and extracted with ether prior to acidification to pH 2 with 2 M HCl followed by extraction with ethyl acetate (2×). The combined ethyl acetate extracts were washed with brine, dried (Na2SO4), and concentrated to afford (1R,2R)-2-2-bromophenyl)-5,5-difluorocyclohexanecarboxylic acid as a tan foam.

Workup

  1. extractionextracted with ether
  2. extractionto acidification to pH 2 with 2 M HCl followed by extraction with ethyl acetate (2×)
  3. washThe combined ethyl acetate extracts were washed with brine
  4. dry with materialdried (Na2SO4)
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-6cb9f4499fcb442c93c87512fb9559af
Source dataset
uspto-grants-2008_07
Patent number
US07405229B2

Reaction notes

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