Potassium Carbonate → 3-Phenylbenzo[b]thiophene-2-carboxylic acid methyl ester

HRID 1186705

Reaction equation

F[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]([C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)=O.[SH:16][CH2:17][C:18]([O:20][CH3:21])=[O:19].C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C>[C:10]1([C:8]2[C:3]3[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=3[S:16][C:17]=2[C:18]([O:20][CH3:21])=[O:19])[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1

Participants

Conditions

Temperature: 70 °C

Procedure

To a stirring solution of (2-fluorophenyl)(phenyl)methanone 87 (2 g, 9.99 mmol) and methyl 2-mercaptoacetate in DMF (30 mL) was added potassium carbonate (4.14 g, 30.0 mmol) and the reaction mixture was stirred at 70° C. for 16 h. The solvent was removed under reduced pressure and the resulting residue was diluted with ethyl acetate and washed with water. The organic layer was dried over Na2SO4, filtered and concentrated under reduced pressure to afford methyl 3-phenylbenzo[b]thiophene-2-carboxylate 88 as a white oily solid (0.62 g, 23% yield) after purification by ISCO (0 to 40% ethyl acetate in hexane). LRMS (ESI): (calc) 268.33 (found) 269.156 (MH)+

Workup

customThe solvent was removed under reduced pressure
additionthe resulting residue was diluted with ethyl acetate
washwashed with water
dry with materialThe organic layer was dried over Na2SO4
filtrationfiltered
concentrationconcentrated under reduced pressure

Sources & evidence

ORD record: ord-230ec06c43ee4cfe8bc693c3daad4eb5
Source dataset: uspto-grants-2014_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08673911B2

Linked notes

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