Dibromodifluoromethane → Benzyl 6,6-difluoro-5-methyl-5-hexenoate

HRID 6468

Reaction equation

HRID 6468 reaction equation
CN(P(N(C)C)N(C)C)C.Br[C:12](Br)([F:14])[F:13].O=[C:17]([CH3:31])[CH2:18][CH2:19][CH2:20][C:21]([O:23][CH2:24][C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1)=[O:22]>COCCOCCOC>[F:13][C:12]([F:14])=[C:17]([CH3:31])[CH2:18][CH2:19][CH2:20][C:21]([O:23][CH2:24][C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1)=[O:22]

Participants

5

Reactant 3

HCID 6382DibromodifluoromethaneHCID 15355Hexamethylphosphorous triamideHCID 12473771Benzyl 5-oxohexanoate

Product 1

HCID 19793833Benzyl 6,6-difluoro-5-methyl-5-hexenoate

Reagents, catalysts & solvents 1

HCID 8150DiglymeSolvent2×

Procedure

27.85 g Tris(dimethylamino)phosphine was added dropwise to a solution of 17.90 g dibromodifluoromethane in 130 ml diglyme, maintained under a nitrogen atmosphere and ice bath cooling. After stirring for one hour on the ice bath, 8.82 g benzyl 5-oxohexanoate in 70 ml diglyme was added slowly, dropwise. The ice bath was then removed and the reaction mixture stirred for 3 hours at room temperature, allowed to stand overnight, poured into 200 ml ice water and extracted with ether. The ether phase was washed twice with water, dried over sodium sulphate, filtered and concentrated in a rotary evaporator. The residue was distilled under reduced pressure.

Workup

  1. temperaturemaintained under a nitrogen atmosphere
  2. temperatureice bath cooling
  3. additionwas added slowly
  4. customThe ice bath was then removed
  5. waitto stand overnight
  6. additionpoured into 200 ml ice water
  7. extractionextracted with ether
  8. washThe ether phase was washed twice with water
  9. dry with materialdried over sodium sulphate
  10. filtrationfiltered
  11. concentrationconcentrated in a rotary evaporator
  12. distillationThe residue was distilled under reduced pressure

Sources & evidence

ORD record
ord-7f55e0a2549a42539e09fd9289ec2f3a
Source dataset
uspto-grants-1993_09
Patent number
US05248810

Linked notes

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