Dimethyl Sulfoxide → 5-(4-Fluorophenoxy)thiophene-2-carbonitrile

HRID 640342

Reaction equation

CS(C)=O.[N+]([C:8]1[S:12][C:11]([C:13]#[N:14])=[CH:10][CH:9]=1)([O-])=O.[F:15][C:16]1[CH:21]=[CH:20][C:19]([OH:22])=[CH:18][CH:17]=1.C(=O)([O-])[O-].[K+].[K+]>O>[F:15][C:16]1[CH:21]=[CH:20][C:19]([O:22][C:8]2[S:12][C:11]([C:13]#[N:14])=[CH:10][CH:9]=2)=[CH:18][CH:17]=1

Participants

Conditions

Temperature: 60 °C

Procedure

To a dimethyl sulfoxide (100 mL) solution of 5-nitro-2-thiophene carbonitrile (5.00 g, 32.4 mmol) were added 4-fluorophenol (5.45 g, 48.6 mmol) and potassium carbonate (11.2 g, 81.0 mmol) under nitrogen atmosphere, which was stirred for 16 hours at 60° C. The reaction solution was cooled to room temperature and water was added, followed by extraction with ethyl acetate. The organic layer was washed with saturated aqueous sodium chloride, and the solvent was evaporated under a reduced pressure. The residue was purified by NH silica gel column chromatography (ethyl acetate:heptane=1:10→1:5) to obtain the title compound (6.10 g, 85.9%).

Workup

temperatureThe reaction solution was cooled to room temperature
extractionfollowed by extraction with ethyl acetate
washThe organic layer was washed with saturated aqueous sodium chloride
customthe solvent was evaporated under a reduced pressure
customThe residue was purified by NH silica gel column chromatography (ethyl acetate:heptane=1:10→1:5)

Sources & evidence

ORD record: ord-6a99905788ad4140bd2ffd2f0a2ea9e8
Source dataset: uspto-grants-2010_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07691882B2

Linked notes

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