Diethyl Ether → (2,5-Dichlorothiophen-3-yl)(phenyl)methanone

HRID 2121719Notes

Reaction equation

[Cl:1][C:2]1[S:3][C:4]([Cl:13])=[CH:5][C:6]=1[C:7](N(OC)C)=[O:8].[C:14]1([Mg]Br)[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1.C(OCC)C.[Cl-].[NH4+]>C1COCC1>[C:7]([C:6]1[CH:5]=[C:4]([Cl:13])[S:3][C:2]=1[Cl:1])(=[O:8])[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1

Participants

Conditions

Temperature: -30 °C

Procedure

To a stirred solution of 2,5-dichloro-N-methoxy-N-methyl-3-thiophenecarboxamide (350 mg, 1.46 mmol) in THF (5 mL) was added 3M solution of phenylmagnesium bromide in diethyl ether (1.2 mL, 3.6 mmol) at −78° C., and the mixture was stirred for 4 hours at −30° C. Saturated ammonium chloride solution was added, and the whole was extracted with ethyl acetate (60 mL×2). The combined organic layers were washed with saturated NaHCO3 solution, brine, dried over MgSO4, and concentrated in vacuo. The resulting residue was purified by flash chromatography eluting with hexane-ethyl acetate (12:1) to provide the title product as a yellow oil. (212 mg, 56% yield).

Workup

extractionthe whole was extracted with ethyl acetate (60 mL×2)
washThe combined organic layers were washed with saturated NaHCO3 solution, brine
dry with materialdried over MgSO4
concentrationconcentrated in vacuo
customThe resulting residue was purified by flash chromatography
washeluting with hexane-ethyl acetate (12:1)

Sources & evidence

ORD record: ord-89f79fed30624ac1aa375443e0615d48
Source dataset: uspto-grants-2004_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06696470B2

Reaction notes

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