Thionyl Chloride → 1-Chloro-3-(chlorophenylmethyl)benzene

Reaction equation

[Cl:1][C:2]1[CH:3]=[C:4]([CH:8]([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)O)[CH:5]=[CH:6][CH:7]=1.S(Cl)([Cl:18])=O>>[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([CH:8]([Cl:18])[C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)[CH:3]=1

Participants

Reactant 2

HCID 24386Thionyl Chloride

HCID 569907(3-Chlorophenyl)(phenyl)methanol

Product 1

HCID 834001-Chloro-3-(chlorophenylmethyl)benzeneYield 37%

Procedure

A solution of (3-chlorophenyl)(phenyl)methanol (500 mg, 2.3 mmol) in thionyl chloride (3 mL) was stirred at 80° C. for 16 h. After cooling to room temperature, the reaction mixture was concentrated and purified by silica gel column (eluting with petroleum ether/ethyl acetate=100/1) to give the desired product (200 mg, 37%) as yellow oil.

Workup

concentrationthe reaction mixture was concentrated
custompurified by silica gel column (eluting with petroleum ether/ethyl acetate=100/1)

Sources & evidence

ORD record: ord-14dc9776f61a4b998d0337704f97a913
Source dataset: uspto-grants-2015_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08952169B2

Reaction notes

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