Water → 4-Difluoromethylene-cyclohexanecarboxylic acid benzyl ester

HRID 1755061Notes

Reaction equation

HRID 1755061 reaction equation
CN(P(N(C)C)(N(C)C)=O)C.[CH2:12]([O:19][C:20]([CH:22]1[CH2:27][CH2:26][C:25](=O)[CH2:24][CH2:23]1)=[O:21])[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.[C:29](Br)(Br)([F:31])[F:30].O>C1COCC1>[CH2:12]([O:19][C:20]([CH:22]1[CH2:27][CH2:26][C:25](=[C:29]([F:31])[F:30])[CH2:24][CH2:23]1)=[O:21])[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1

Participants

6

Reactant 4

HCID 962WaterHCID 6382DibromodifluoromethaneHCID 12679HexamethylphosphoramideHCID 15395052Benzyl 4-oxocyclohexane-1-carboxylate

Product 1

HCID 668178704-Difluoromethylene-cyclohexanecarboxylic acid benzyl esterYield 9.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

HMPT (7.40 ml, 39.5 mmol) was added to a solution of 4-oxo-cyclohexanecarboxylic acid benzyl ester (1.50 g, 6.59 mmol) and CF2Br2 (1.8 ml, 19.8 mmol) in THF (30 ml) at 0° C., and the reaction mixture was stirred at room temperature for 22 hours. Water was added, followed by extraction with ethyl acetate. The organic layer was then dried over MgSO4 and concentrated under reduced pressure. The resulting residue was purified by silica gel column chromatography (hexane/ethyl acetate=100/0→75/25) to give 4-difluoromethylene-cyclohexanecarboxylic acid benzyl ester (166 mg, 9%).

Workup

  1. extractionfollowed by extraction with ethyl acetate
  2. dry with materialThe organic layer was then dried over MgSO4
  3. concentrationconcentrated under reduced pressure
  4. customThe resulting residue was purified by silica gel column chromatography (hexane/ethyl acetate=100/0→75/25)

Sources & evidence

ORD record
ord-aa9760664e29433aa785833801980ef9
Source dataset
uspto-grants-2015_10
Patent number
US09169254B2

Reaction notes

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