Thionyl Chloride → 2-(Chloromethyl)-4-(trifluoromethyl)thiophene

Reaction equation

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

Participants

Reactant 2

HCID 24386Thionyl Chloride

HCID 896902462-Thiophenemethanol, 4-(trifluoromethyl)-

Product 1

HCID 1177986592-(Chloromethyl)-4-(trifluoromethyl)thiopheneYield 49.9%

Procedure

Thionyl chloride (4.89 g) was added to [4-(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 (275 mg).

Workup

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

Sources & evidence

ORD record: ord-ac6344eb7cb448d9bef47e52838f57dd
Source dataset: uspto-grants-2015_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09199963B2

Reaction notes

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