Hexane → 1,1-Dibromo-2-[2-chloro-4-(methylsulphenyl)phenyl]ethene
Reaction equation
[C:1]1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[C:20]([Br:24])(Br)(Br)[Br:21].[Cl:25][C:26]1[CH2:33][C:32](=[S:34])[CH:31]=[CH:30][C:27]=1[CH:28]=O.CCCCCC>ClCCl>[Br:21][C:20]([Br:24])=[CH:28][C:27]1[CH:30]=[CH:31][C:32]([S:34][CH3:1])=[CH:33][C:26]=1[Cl:25]Participants
6
Procedure
Triphenyl phosphine (2.5 g) was added to a stirred solution of carbon tetrabromide (1.48 g) in dichloromethane maintaining the temperature at 0° C. The mixture was stirred for 0.5 hours and 2-chloro-4-(sulphenyl)-benzaldehyde (1.0 g) was added. The resultant mixture was stirred for 0.5 hours and poured into hexane. The resulting solid was filtered off and washed with ether. The combined filtrates were evaporated to dryness and the residue was purified by chromatrography eluted with hexane to give 1,1-dibromo-2-[2-chloro-4-(methylsulphenyl)phenyl]ethene (0.96 g) as a white solid, NMR (CDCl3) 2.45 (s,3H), 7.15(d,1H), 7.25(s,1H), 7.55(s,1H), 7.6(d,1H).
Workup
- filtrationThe resulting solid was filtered off
- washwashed with ether
- customThe combined filtrates were evaporated to dryness
- customthe residue was purified by chromatrography
- washeluted with hexane
Sources & evidence
- ORD record
- ord-83fe531f4476447f9aae62051afdd24b
- Source dataset
- uspto-grants-1994_11
- Patent number
- US05366957
Reaction notes
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