Thionyl Chloride → 4-(4-Trifluoromethylphenyl)benzylchloride

HRID 1913766Notes

Reaction equation

HRID 1913766 reaction equation
S(Cl)([Cl:3])=O.[F:5][C:6]([F:22])([F:21])[C:7]1[CH:12]=[CH:11][C:10]([C:13]2[CH:18]=[CH:17][C:16]([CH2:19]O)=[CH:15][CH:14]=2)=[CH:9][CH:8]=1>C(Cl)(Cl)Cl>[Cl:3][CH2:19][C:16]1[CH:17]=[CH:18][C:13]([C:10]2[CH:11]=[CH:12][C:7]([C:6]([F:22])([F:21])[F:5])=[CH:8][CH:9]=2)=[CH:14][CH:15]=1

Participants

4

Reactant 2

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

Product 1

HCID 114599214-(4-Trifluoromethylphenyl)benzylchlorideYield 98%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent2×

Procedure

2.89 ml (39.65 mmol) of thionyl chloride dissolved in 10 ml of chloroform are added to a solution of 5.0 g (19.82 mmol) of (4′-trifluoromethylbiphenyl-4-yl)methanol in 40 ml of chloroform, and the mixture is stirred at room temperature for 12 hours. After reaction is complete, the reaction mixture is evaporated to dryness, and the residue is taken up in ethyl acetate and washed with saturated sodium carbonate solution. The organic phase is separated off, dried over sodium sulphate and evaporated after filtration. The resulting crude product is purified by flash chromatography on silica gel (mobile phase: cyclohexane/ethyl acetate 9:1). 5.26 g (19.43 mmol, 98% yield) of a colourless solid are obtained.

Workup

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

Sources & evidence

ORD record
ord-094c11a69d28425baccba49efd3ec264
Source dataset
uspto-grants-2013_12
Patent number
US08609727B2

Reaction notes

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