Ammonium Chloride → 2-Acetylamino-5-benzyl-7-hydroxy-benzo[b]thiophene-3-carboxylic acid ethyl ester

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Reaction Steps

A flame dried three-necked flask was purged with N2 and charged with bromide 01-5 (3.35 g, 7.4 mmol), LiBr (707 mg, 8.2 mmol, 1.1 equiv.), Li2CO3 (601 mg, 8.2 mmol, 1.1 equiv.) and DMF (85 mL). The resulting suspension was refluxed overnight under N2-atmosphere. The reaction mixture was cooled to RT and poured into saturated aqueous NH4Cl (500 mL). The aqueous layer was extracted with EtOAc (3×100 mL). The combined organic layers were washed with H2O (3×200 mL), brine (200 mL) and dried over Na2SO4. The solvent was removed in vacuo to give the crude product as a brownish solid. The solid was washed with Et2O (25 mL) to give 01-6 (2.1 g, 5.7 mmol, 77%) as a slightly brown solid.

Provenance & Evidence