Water → 1,2-Difluoro-4-(2-methoxy-vinyl)-benzene
Reaction equation
CC(C)([O-])C.[K+].[Cl-].[CH3:8][O:9][CH2:10][P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.[F:30][C:31]1[CH:32]=[C:33]([CH:36]=[CH:37][C:38]=1[F:39])[CH:34]=O.O>C1COCC1>[F:39][C:38]1[CH:37]=[CH:36][C:33]([CH:34]=[CH:8][O:9][CH3:10])=[CH:32][C:31]=1[F:30]Participants
Procedure
Potassium tert butoxide (11 g, 0.098 mol) was added to methoxymethyl triphenyl phosphonium chloride (31.12 g, 0.091 mol) in 150 ml of dry THF at −30° C. under argon atmosphere and stirred for 1 h. 3,4-difluorobenzaldehyde (10 g, 0.07 mol) in 60 ml of THF was added dropwise at the same temperature and stirring continued for 3 h at room temperature. The reaction mixture was treated with 100 ml water, 150 ml petroleum ether and filtered through celite. Organic layer was separated and aq. layer was extracted with petroleum ether (2×100 ml). Combined organic layer was washed with brine and dried over sodium sulfate. Solvent evaporation under reduced pressure followed by purification over silica gel using petroleum ether as eluent afforded (5.5 g) of the sub-titles compound as a colorless liquid.
Workup
- stirringstirring
- waitcontinued for 3 h at room temperature
- filtrationfiltered through celite
- customOrganic layer was separated
- extractionaq. layer was extracted with petroleum ether (2×100 ml)
- washCombined organic layer was washed with brine
- dry with materialdried over sodium sulfate
- customSolvent evaporation under reduced pressure
- customfollowed by purification over silica gel
Sources & evidence
- ORD record
- ord-7570f9f2caf94e8eb3dc1be230cc81cb
- Source dataset
- uspto-grants-2010_01
- Patent number
- US07648985B2
Reaction notes
Loading…