Thionyl Chloride → 2-(Chloromethyl)-5-(trifluoromethyl)thiophene

HRID 1497410Notes

Reaction equation

HRID 1497410 reaction equation
S(Cl)([Cl:3])=O.[F:5][C:6]([F:15])([F:14])[C:7]1[S:11][C:10]([CH2:12]O)=[CH:9][CH:8]=1>>[Cl:3][CH2:12][C:10]1[S:11][C:7]([C:6]([F:15])([F:14])[F:5])=[CH:8][CH:9]=1

Participants

3

Reactant 2

HCID 24386Thionyl ChlorideHCID 539255405-(Trifluoromethyl)-2-thiophenemethanol

Product 1

HCID 545735382-(Chloromethyl)-5-(trifluoromethyl)thiopheneYield 52.5%

Procedure

Thionyl chloride (4.89 g) was added to [5-(trifluoromethyl)thiophen-2-yl]methanol (500 mg) at room temperature, and the mixture was stirred for 3 hr. The reaction mixture was concentrated, and the obtained residue was purified by silica gel column chromatography (hexane/ethyl acetate) to give the title compound (289 mg).

Workup

  1. concentrationThe reaction mixture was concentrated
  2. customthe obtained residue was purified by silica gel column chromatography (hexane/ethyl acetate)

Sources & evidence

ORD record
ord-f742515fb9104eb3801d9c1ae95de46d
Source dataset
uspto-grants-2015_12
Patent number
US09199963B2

Reaction notes

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