Dimethylformamide → 4,4'-Dichlorobenzhydryl chloride

HRID 2278160Notes

Reaction equation

HRID 2278160 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([C:10]2[CH:15]=[CH:14][C:13]([Cl:16])=[CH:12][CH:11]=2)O)=[CH:4][CH:3]=1.CN(C)C=O.S(Cl)([Cl:24])=O>ClCCl>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([Cl:24])[C:10]2[CH:15]=[CH:14][C:13]([Cl:16])=[CH:12][CH:11]=2)=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 70334,4'-DichlorobenzhydrolHCID 24386Thionyl Chloride

Product 1

HCID 130784,4'-Dichlorobenzhydryl chlorideYield 89.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
40 °C

Procedure

A 1000 mL 3-necked round-bottom flask was charged with bis(4-chlorophenyl)methanol (49.6 g, 196 mmol, 1.00 equiv), N,N-dimethylformamide (5 mL), dichloromethane (100 mL). Liquid thionyl chloride (93.3 g, 790 mmol, 4.00 equiv) was added dropwise. The resulting solution was stirred overnight at 40° C. in an oil bath. The resulting mixture was concentrated under reduced pressure. The residue was chromatographed on a silica gel column with ethyl acetate/petroleum ether (1/5) to provide 47.8 g (88% yield) of 1-chloro-4-[chloro(4-chlorophenyl)methyl]benzene as a gray solid. 1HNMR 300 MHz (CDCl3) δ 7.30-7.39 (m, 8H), 6.07 (s, 1H). GCMS (EI, m/z): 270 [M]+.

Workup

  1. concentrationThe resulting mixture was concentrated under reduced pressure
  2. customThe residue was chromatographed on a silica gel column with ethyl acetate/petroleum ether (1/5)

Sources & evidence

ORD record
ord-283b73a813ed474abed33d875ebc7158
Source dataset
uspto-grants-2015_09
Patent number
US09133148B2

Reaction notes

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