Carbon Tetrachloride → 4-(Benzylsulfanyl)benzyl chloride

HRID 1644696Notes

Reaction equation

HRID 1644696 reaction equation
C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[C:20]([Cl:24])(Cl)(Cl)Cl.[CH2:25]([S:32][C:33]1[CH:38]=[CH:37][C:36](CO)=[CH:35][CH:34]=1)[C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1>O1CCCC1>[CH2:25]([S:32][C:33]1[CH:38]=[CH:37][C:36]([CH2:20][Cl:24])=[CH:35][CH:34]=1)[C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1

Participants

5

Reactant 3

HCID 5943Carbon TetrachlorideHCID 11776TriphenylphosphineHCID 4349993[4-(Benzylsulfanyl)phenyl]methanol

Product 1

HCID 593508264-(Benzylsulfanyl)benzyl chlorideYield 67%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Triphenylphosphine (14.9 g, 56.8 mmol), carbon tetrachloride (35 mL, 360 mmol), (4-benzylsulfanyl-phenyl)-methanol (6.33 g, 27.5 mmol), and tetrahydrofuran (120 mL) were combined and stirred at reflux temperature overnight. The reaction mixture was cooled to room temperature, then partitioned between ethyl acetate and water (750 mL). The organic phase was dried over MgSO4, filtered, and concentrated to give the crude product. Flash chromatography (Analogix SuperFlash™ column, 100% hexanes -25% ethyl acetate in hexanes) afforded 4.57 g (67%) of 4-(benzylsulfanyl)benzyl chloride as an off-white solid. 1H NMR (300 MHz, DMSO-d6) δ ppm 7.16-7.44 (m, 9 H), 4.72 (s, 2 H), 4.26 (s, 2 H).

Workup

  1. temperatureat reflux temperature overnight
  2. custompartitioned between ethyl acetate and water (750 mL)
  3. dry with materialThe organic phase was dried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customto give the crude product

Sources & evidence

ORD record
ord-3c2b7748619f4afe83c62b3f79150dbf
Source dataset
uspto-grants-2012_02
Patent number
US08124629B2

Reaction notes

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