Thionyl Chloride → 3-(4-Trifluoromethylphenyl)-benzyl chloride

HRID 1993022Notes

Reaction equation

HRID 1993022 reaction equation
[F:1][C:2]([F:18])([F:17])[C:3]1[CH:8]=[CH:7][C:6]([C:9]2[CH:10]=[C:11]([CH:14]=[CH:15][CH:16]=2)[CH2:12]O)=[CH:5][CH:4]=1.S(Cl)([Cl:21])=O>ClCCl>[F:1][C:2]([F:18])([F:17])[C:3]1[CH:8]=[CH:7][C:6]([C:9]2[CH:10]=[C:11]([CH:14]=[CH:15][CH:16]=2)[CH2:12][Cl:21])=[CH:5][CH:4]=1

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 144680034'-(Trifluoromethyl)[1,1'-biphenyl]-3-methanol

Product 1

HCID 222801383-(4-Trifluoromethylphenyl)-benzyl chloride

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

The alcohol 2.2 (15 g, 59.5 mmol) was dissolved in anhydrous dichloromethane (100 mL). Thionyl chloride (10 mL) was slowly added dropwise to the above solution. The resulting mixture was stirred at room temperature for 24 hours. The organic solvent was removed under vacuo. The residue was then purified by flash chromatography (SiO2 gel 60, eluted with 20% DCM in hexanes). Fractions containing the desired product 2.3 were combined and concentrated to a white solid (14.0 g). 1H NMR (400 MHz) (CDCl3) δ 7.73 (4H, s); 7.65 (1H, s); 7.58 (1H, s); 7.52-7.28 (2H, m); 4.69 (2H, s).

Workup

  1. customThe organic solvent was removed under vacuo
  2. customThe residue was then purified by flash chromatography (SiO2 gel 60, eluted with 20% DCM in hexanes)
  3. additionFractions containing the desired product 2.3
  4. concentrationconcentrated to a white solid (14.0 g)

Sources & evidence

ORD record
ord-53bca3548f004094b503e58e474e7a18
Source dataset
uspto-grants-2010_01
Patent number
US07649110B2

Reaction notes

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