4,4-Difluorocyclohexanone → 1,1-Difluoro-4-methylidenecyclohexane

HRID 2040886Notes

Reaction equation

HRID 2040886 reaction equation
[Br-].[CH3:2][P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.[NH2-].[Na+].[F:24][C:25]1([F:32])[CH2:30][CH2:29][C:28](=O)[CH2:27][CH2:26]1>CCOCC>[F:24][C:25]1([F:32])[CH2:30][CH2:29][C:28](=[CH2:2])[CH2:27][CH2:26]1

Participants

4

Reactant 2

HCID 157890924,4-DifluorocyclohexanoneHCID 16212304Sodium;azanide;methyl(triphenyl)phosphanium;bromide

Product 1

HCID 574938571,1-Difluoro-4-methylidenecyclohexane

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

A methyl triphenyl phosphonium bromide/sodium amide mixture (MTP instant ylide, 0.49 g, 1.24 mmol) was suspended in anhydrous Et2O (3 mL) stirring for 1 h at r.t. Afterwards, the reaction mixture was cooled at 0° C. and a solution of 4,4-difluorocyclohexanone (0.145 g, 1.08 mmol) in 3 mL of Et2O was added dropwise into. Stirring at r.t. was maintained for 16 h, then the reaction mixture was filtered and the filtrate was used in the next step without further purification.

Workup

  1. temperatureAfterwards, the reaction mixture was cooled at 0° C.
  2. stirringStirring at r.t.
  3. temperaturewas maintained for 16 h
  4. filtrationthe reaction mixture was filtered
  5. customthe filtrate was used in the next step without further purification

Sources & evidence

ORD record
ord-da2b312612ef4c0da124c1770a5eadf9
Source dataset
uspto-grants-2013_11
Patent number
US08580962B2

Reaction notes

Loading…