Thionyl Chloride → 1-(chloro(phenyl)methyl)-3-(trifluoromethyl)benzene

HRID 1926665Notes

Reaction equation

HRID 1926665 reaction equation
[F:1][C:2]([F:18])([F:17])[C:3]1[CH:4]=[C:5]([CH:14]=[CH:15][CH:16]=1)[CH:6](O)[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1.S(Cl)([Cl:21])=O>C(Cl)Cl>[Cl:21][CH:6]([C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1)[C:5]1[CH:14]=[CH:15][CH:16]=[C:3]([C:2]([F:18])([F:17])[F:1])[CH:4]=1

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 27774043-(Trifluoromethyl)benzhydrol

Product 1

HCID 5968291-(chloro(phenyl)methyl)-3-(trifluoromethyl)benzeneYield 90.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
50 °C

Procedure

To a solution of 3-(trifluoromethyl)benzhydrol (5 mL, 20 mmol) in CH2Cl2 (10 mL) was added dropwise thionyl chloride (3 mL, 41 mmol) at rt. The reaction was stirred at 50° C. for 18 h, concentrated under vacuum, azeotroped with toluene and dried under vacuum to give the title compound (4.9 g, 89% yield) as oil, which was used in the next step without further purification. MS (ESI, pos. ion) m/z: 235.0 (M-HCl).

Workup

  1. concentrationconcentrated under vacuum
  2. customazeotroped with toluene
  3. customdried under vacuum

Sources & evidence

ORD record
ord-1e59f82beeba42949a0158c5c0e554fb
Source dataset
uspto-grants-2012_05
Patent number
US08183244B2

Reaction notes

Loading…