Thionyl Chloride → 4-(4-Trifluoromethylphenyl)benzylchloride

HRID 1921871Notes

Reaction equation

HRID 1921871 reaction equation
[F:1][C:2]([F:18])([F:17])[C:3]1[CH:8]=[CH:7][C:6]([C:9]2[CH:14]=[CH:13][C:12]([CH2:15]O)=[CH:11][CH:10]=2)=[CH:5][CH:4]=1.S(Cl)([Cl:21])=O>C(Cl)(Cl)Cl>[Cl:21][CH2:15][C:12]1[CH:13]=[CH:14][C:9]([C:6]2[CH:7]=[CH:8][C:3]([C:2]([F:18])([F:17])[F:1])=[CH:4][CH:5]=2)=[CH:10][CH:11]=1

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 22015014(4'-(Trifluoromethyl)-[1,1'-biphenyl]-4-yl)methanol

Product 1

HCID 114599214-(4-Trifluoromethylphenyl)benzylchloride

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent2×

Procedure

A solution of 5.00 g (19.8 mmol) of (4′-trifluoromethylbiphenyl-4-yl)methanol in 40 ml of chloroform is mixed with 2.89 ml (39.7 mmol) of thionyl chloride dissolved in 10 ml of chloroform, and the mixture is stirred at room temperature over 12 hours. After reaction is complete, the reaction mixture is concentrated to dryness, and the residue is taken up ethyl acetate and washed with saturated sodium carbonate solution. The organic phase is subsequently separated off, dried over sodium sulfate and concentrated after filtration. The resulting crude product is purified by flash chromatography on silica gel 60 (mobile phase: cyclohexane/ethyl acetate 9:1). 5.26 g (19.4 mmol, 98% of theory) of the title compound are obtained.

Workup

  1. customAfter reaction
  2. concentrationthe reaction mixture is concentrated to dryness
  3. washwashed with saturated sodium carbonate solution
  4. customThe organic phase is subsequently separated off
  5. dry with materialdried over sodium sulfate
  6. concentrationconcentrated
  7. filtrationafter filtration
  8. customThe resulting crude product is purified by flash chromatography on silica gel 60 (mobile phase: cyclohexane/ethyl acetate 9:1)

Sources & evidence

ORD record
ord-3f4f417d7ea64f87a4e6c1819f5bc278
Source dataset
uspto-grants-2012_05
Patent number
US08173704B2

Reaction notes

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