Potassium Carbonate → 6-Iodo-benzo[b]thiophene-2-carboxylic acid ethyl ester

HRID 599671Notes

Reaction equation

F[C:2]1[C:9]([Si](C)(C)C)=[C:8]([I:14])[CH:7]=[CH:6][C:3]=1[CH:4]=O.[CH2:15]([O:17][C:18](=[O:21])[CH2:19][SH:20])[CH3:16].C([O-])([O-])=O.[K+].[K+]>CN(C=O)C>[CH2:15]([O:17][C:18]([C:19]1[S:20][C:2]2[CH:9]=[C:8]([I:14])[CH:7]=[CH:6][C:3]=2[CH:4]=1)=[O:21])[CH3:16]

Participants

Conditions

Temperature: 75 °C

Procedure

A solution of 2-fluoro-4-iodo-3-trimethylsilanyl-benzaldehyde (14.2 g, 44.1 mmol) (Tetrahedron Letters 1992, p 7499-7502) in DMF (50 mL) is treated with mercapto-acetic acid ethyl ester (5.80 mL, 52.9 mmol) and K2CO3 (12.2 g, 88.2 mmol). The resulting suspension is stirred at 75° C. for 60 min and quenched with water (300 mL). The mixture is extracted with EtOAc (3×50 mL,) and the organic layer is dried over Na2SO4, concentrated, and purified by silica gel column chromatography (5-20% EtOAc/Hex), to give the title compound as an oil (9.40 g, 64%).

Workup

customquenched with water (300 mL)
extractionThe mixture is extracted with EtOAc (3×50 mL,)
dry with materialthe organic layer is dried over Na2SO4
concentrationconcentrated
custompurified by silica gel column chromatography (5-20% EtOAc/Hex)

Sources & evidence

ORD record: ord-491dd30cc7264acebdd180db6ce062b3
Source dataset: uspto-grants-2011_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07897789B2

Reaction notes

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