1-Bromo-4-fluorobenzene → 2-(3,5-Dichloro-4'-fluoro-2-[1,1'-biphenyl]yl)-4,4-dimethyl-2-oxazoline
Reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([Mg]Br)=[CH:4][CH:3]=1.FC1C=CC(Br)=CC=1.[Mg].[Cl:19][C:20]1[CH:25]=[C:24]([Cl:26])[CH:23]=[C:22](OC)[C:21]=1[C:29]1[O:30][CH2:31][C:32]([CH3:35])([CH3:34])[N:33]=1>C1COCC1>[Cl:19][C:20]1[C:21]([C:29]2[O:30][CH2:31][C:32]([CH3:35])([CH3:34])[N:33]=2)=[C:22]([C:5]2[CH:6]=[CH:7][C:2]([F:1])=[CH:3][CH:4]=2)[CH:23]=[C:24]([Cl:26])[CH:25]=1Participants
6
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Procedure
4-Fluorophenylmagnesium bromide, prepared from 4-fluorobromobenzene (120 mmol) and magnesium (120 mmol), in dry THF (75 ml) was added dropwise to a stirred solution of 2-(2,4-dichloro-6-methoxyphenyl)-4,4-dimethyl-2-oxazoline (100 mmol) in dry THF (150 ml) under N2 at 20° C. Stirring of the solution was continued for 20 hours and then the reaction mixture was quenched by the addition of saturated ammonium chloride solution. The resulting mixture was extracted with ether (2×500 ml), dried over MgSO4, filtered and evaporated. The residue was chromatographed on silica gel (ethyl acetatehexane) to provide title compound (85%), mp 93°-95° C.
Workup
- customthe reaction mixture was quenched by the addition of saturated ammonium chloride solution
- extractionThe resulting mixture was extracted with ether (2×500 ml)
- dry with materialdried over MgSO4
- filtrationfiltered
- customevaporated
- customThe residue was chromatographed on silica gel (ethyl acetatehexane)
Sources & evidence
- ORD record
- ord-6a1e8ca51f7e41bf8b9aee9bd0401a08
- Source dataset
- uspto-grants-1981_12
- Patent number
- US04308378
Reaction notes
Loading…