Carbon Tetrachloride → 2-(Benzenesulfonyl)benzyl chloride

HRID 1644702Notes

Reaction equation

HRID 1644702 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][CH:37]=[CH:36][C:35]=2CO)(=[O:33])=[O:32])[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1.O1CCCC1>O>[C:25]1([S:31]([C:34]2[CH:39]=[CH:38][CH:37]=[CH:36][C:35]=2[CH2:20][Cl:24])(=[O:33])=[O:32])[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=1

Participants

6

Reactant 4

HCID 5943Carbon TetrachlorideHCID 8028TetrahydrofuranHCID 11776TriphenylphosphineHCID 59350822HCID 59350822, compound

Product 1

HCID 538274902-(Benzenesulfonyl)benzyl chlorideYield 85%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Triphenylphosphine (4.08 g, 15.5 mmol), carbon tetrachloride (7.0 mL, 73 mmol), (2-benzenesulfonyl-phenyl)-methanol (1.90 g, 7.65 mmol) and tetrahydrofuran (40 mL) were combined and heated at reflux for 2 hours. The reaction mixture was cooled to room temperature, then stirred at room temperature for 60 hours. The reaction mixture was diluted with water, then extracted three times with ethyl acetate. The combined organic phases were washed with brine, 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 (0%-15% ethyl acetate in hexanes) afforded 1.73 g (85%) of 2-(benzenesulfonyl)benzyl chloride as an off-white, crystalline solid. 1H NMR (300 MHz, DMSO-d6) δ ppm 8.14 (d, J=7.8 Hz, 1 H), 7.93 (d, J=7.2 Hz, 2 H), 7.56-7.82 (m, 6 H), 5.07 (s, 2 H). HRMS (EI+) cald. for C13H11ClO2S [M+] 266.0168, obsd. 266.0168.

Workup

  1. temperatureheated
  2. temperatureat reflux for 2 hours
  3. extractionextracted three times with ethyl acetate
  4. washThe combined organic phases were washed with brine
  5. dry with materialdried over MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customto give the crude product as an oily solid
  9. customA solution of this crude product and dichloromethane was evaporated over silica gel

Sources & evidence

ORD record
ord-e4884bd5788745be9a407f1b3b570363
Source dataset
uspto-grants-2012_02
Patent number
US08124629B2

Reaction notes

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