Thionyl Chloride → 4-(Methylthio)-3-(trifluoromethyl)benzyl chloride

HRID 452637Notes

Reaction equation

HRID 452637 reaction equation
[CH3:1][S:2][C:3]1[CH:10]=[CH:9][C:6]([CH2:7]O)=[CH:5][C:4]=1[C:11]([F:14])([F:13])[F:12].S(Cl)([Cl:17])=O>C1(C)C=CC=CC=1>[CH3:1][S:2][C:3]1[CH:10]=[CH:9][C:6]([CH2:7][Cl:17])=[CH:5][C:4]=1[C:11]([F:14])([F:13])[F:12]

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 68663620HCID 68663620, compound

Product 1

HCID 686631284-(Methylthio)-3-(trifluoromethyl)benzyl chlorideYield 78.2%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

To a solution of 4-(methylthio)-3-(trifluoromethyl)benzyl alcohol (3.00 g, 13.5 mmol) in toluene (15 mL) was added thionyl chloride (1.18 mL, 16.2 mmol) at room temperature, and the resulting mixture was stirred for 1 hr. The reaction mixture was concentrated under reduced pressure. The residue was purified by basic silica gel column chromatography (hexane/ethyl acetate=10/1), and crystallized from hexane to give the title compound (2.54 g, yield 78%) as colorless crystals.

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. customThe residue was purified by basic silica gel column chromatography (hexane/ethyl acetate=10/1)
  3. customcrystallized from hexane

Sources & evidence

ORD record
ord-fbc4c5979b714003bab4103f73dc3040
Source dataset
uspto-grants-2013_07
Patent number
US08492378B2

Reaction notes

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