Carbon Tetrachloride → 4-(Benzenesulfonyl)benzyl chloride
Reaction equation
C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[C:20]([Cl:24])(Cl)(Cl)Cl.[C:25]1([S:31]([C:34]2[CH:39]=[CH:38][C:37](CO)=[CH:36][CH:35]=2)(=[O:33])=[O:32])[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1>O1CCCC1>[C:25]1([S:31]([C:34]2[CH:39]=[CH:38][C:37]([CH2:20][Cl:24])=[CH:36][CH:35]=2)(=[O:33])=[O:32])[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=1Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 100 °C
Procedure
Triphenylphosphine (5.98 g, 22.8 mmol), carbon tetrachloride (9 mL, 93 mmol), (4-benzenesulfonyl-phenyl)-methanol (2.83 g, 11.4 mmol) and tetrahydrofuran (42 mL) were combined and heated at 100° C. for 4 hours. The reaction mixture was cooled to room temperature, then partitioned between ethyl acetate (100 mL) and water (100 mL). The organic phase was dried over MgSO4, filtered, and concentrated to give the crude product as an oily solid. A solution of this crude product and dichloromethane was evaporated over silica gel, and the resulting silica gel supported crude product was loaded onto an Analogix SuperFlash™ column. Flash chromatography (15%-35% ethyl acetate in hexanes) afforded 3.09 g (100%) of 4-(benzenesulfonyl)benzyl chloride as a white, crystalline solid. 1H NMR (300 MHz, DMSO-d6) δ ppm 7.89-8.04 (m, 4 H), 7.53-7.75 (m, 5 H), 4.81 (s, 2 H).
Workup
- temperatureThe reaction mixture was cooled to room temperature
- custompartitioned between ethyl acetate (100 mL) and water (100 mL)
- dry with materialThe organic phase was dried over MgSO4
- filtrationfiltered
- concentrationconcentrated
- customto give the crude product as an oily solid
- customA solution of this crude product and dichloromethane was evaporated over silica gel
Sources & evidence
- ORD record
- ord-743f64c70db14f888aabdba500ce5dc8
- Source dataset
- uspto-grants-2012_02
- Patent number
- US08124629B2
Reaction notes
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