Water → 2-(Bromomethyl)-4-chloro-1-(methylsulfonyl)benzene
Reaction equation
C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[Br:20]Br.[Cl:22][C:23]1[CH:24]=[CH:25][C:26]([S:31]([CH3:34])(=[O:33])=[O:32])=[C:27]([CH2:29]O)[CH:28]=1.O>C(#N)C>[Br:20][CH2:29][C:27]1[CH:28]=[C:23]([Cl:22])[CH:24]=[CH:25][C:26]=1[S:31]([CH3:34])(=[O:33])=[O:32]Participants
Procedure
(Step 3) Triphenylphosphine (1.19 g) was suspended in acetonitrile (50 ml), bromine (0.24 ml) was added, and the mixture was stirred at room temperature for 30 min. A solution of [5-chloro-2-(methylsulfonyl)phenyl]methanol obtained in Step 2 (1 g) in acetonitrile (10 ml) was added to the reaction mixture. The mixture was stirred at 70° C. for 3 hr, treated with water, and extracted with ethyl acetate. The extract was washed successively with aqueous sodium hydrogen carbonate solution and saturated brine, and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure. The obtained residue was purified by basic silica gel chromatography (ethyl acetate:hexane=1:3) to give 2-(bromomethyl)-4-chloro-1-(methylsulfonyl)benzene (0.46 g).
Workup
- stirringThe mixture was stirred at 70° C. for 3 hr
- extractionextracted with ethyl acetate
- washThe extract was washed successively with aqueous sodium hydrogen carbonate solution and saturated brine
- dry with materialdried over anhydrous magnesium sulfate
- customThe solvent was evaporated under reduced pressure
- customThe obtained residue was purified by basic silica gel chromatography (ethyl acetate:hexane=1:3)
Sources & evidence
- ORD record
- ord-18839e26441946d4b7c37bc1b1638bdb
- Source dataset
- uspto-grants-2011_07
- Patent number
- US07982044B2
Reaction notes
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