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

HRID 2375729Notes

Reaction equation

HRID 2375729 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>C(Cl)Cl>[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 DCM (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 chromatographed (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 chromatographed
  3. wash(SiO2 gel 60, eluted with 20% DCM in hexanes)
  4. additionFractions containing the desired product 2.3
  5. concentrationconcentrated to a white solid (14.0 g)

Sources & evidence

ORD record
ord-949ec55418034563ab0edd6d5205d4e8
Source dataset
uspto-grants-2008_12
Patent number
US07465804B2

Reaction notes

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