Dibromodifluoromethane → Benzyl 8,8-difluoro-7-methyl-7-octenoate

HRID 6472

Reaction equation

HRID 6472 reaction equation
CN(P(N(C)C)N(C)C)C.Br[C:12](Br)([F:14])[F:13].O=[C:17]([CH3:33])[CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][C:23]([O:25][CH2:26][C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1)=[O:24]>COCCOCCOC>[F:13][C:12]([F:14])=[C:17]([CH3:33])[CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][C:23]([O:25][CH2:26][C:27]1[CH:28]=[CH:29][CH:30]=[CH:31][CH:32]=1)=[O:24]

Participants

5

Reactant 3

HCID 6382DibromodifluoromethaneHCID 15355Hexamethylphosphorous triamideHCID 19793826Benzyl 7-oxooctanoate

Product 1

HCID 19793855Benzyl 8,8-difluoro-7-methyl-7-octenoate

Reagents, catalysts & solvents 1

HCID 8150DiglymeSolvent3×

Procedure

123 ml (0.68 mol) Tris(dimethylamino)phosphine in 100 ml diglyme was added slowly dropwise to a solution of 26.3 ml (0.34 mol) dibromodifluoromethane in 800 ml diglyme. After stirring for one hour on an ice bath, 43 g (0.17 mol}benzyl 7-oxooctanoate in 100 ml diglyme was slowly added dropwise. The ice bath was removed and the reaction mixture stirred for 40 minutes at room temperature, poured into 1 liter ice-water and extracted with ether. The ether phase was washed twice with water, dried over sodium sulphate, filtered and concentrated. The residue was purified by column chromatography (silica gel hexane/ether=3:1)

Workup

  1. customThe ice bath was removed
  2. stirringthe reaction mixture stirred for 40 minutes at room temperature
  3. additionpoured into 1 liter ice-water
  4. extractionextracted with ether
  5. washThe ether phase was washed twice with water
  6. dry with materialdried over sodium sulphate
  7. filtrationfiltered
  8. concentrationconcentrated
  9. customThe residue was purified by column chromatography (silica gel hexane/ether=3:1)

Sources & evidence

ORD record
ord-6a9f947d18fd4b718325c2f1fee21eab
Source dataset
uspto-grants-1993_09
Patent number
US05248810

Linked notes

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