2-Chloro-N-methoxy-N-methylacetamide → HCID 22474015, compound

Temperature

-50 °C

A solution of 3-bromo-4-fluorobenzo[b]thiophene (0.76 g) in tetrahydrofuran (5 ml) was added dropwise under nitrogen at −60-−50° C. over 10 minutes to a stirred solution of n-butyllithium (2.5M solution in hexanes; 1.71 ml) in ether (40 ml), then the mixture was stirred at −50° C. for 30 minutes. A solution of 2-chloro-N-methoxy-N-methylacetamide (0.39 g) in tetrahydrofuran (10 ml) was added dropwise over 10 minutes, the mixture was stirred at −50° C. for 30 minutes and at 0° C. for 1 hour, then it was quenched by the addition of saturated aqueous ammonium chloride solution (30 ml). The organic layer was separated, washed with saturated aqueous sodium chloride solution (30 ml), dried (MgSO4) and the solvent was removed in vacuo. The residue was purified by flash chromatography over silica using a 10:1 mixture of petroleum ether (b.p. 60-80° C.) and ethyl acetate as eluant. Appropriate fractions were combined and the solvents removed in vacuo to give 2-chloro-1-(4-fluorobenzo[b]thiophen-2-yl]ethan-1-one (0.1 g) as a colourless solid which was used without further purification.

1. stirringthe mixture was stirred at −50° C. for 30 minutes and at 0° C. for 1 hour
2. customit was quenched by the addition of saturated aqueous ammonium chloride solution (30 ml)
3. customThe organic layer was separated
4. washwashed with saturated aqueous sodium chloride solution (30 ml)
5. dry with materialdried (MgSO4)
6. customthe solvent was removed in vacuo
7. customThe residue was purified by flash chromatography over silica using
8. additiona 10:1 mixture of petroleum ether (b.p. 60-80° C.) and ethyl acetate as eluant
9. customthe solvents removed in vacuo

ORD record

ord-36cdf5ab3eff4415ad6f171d067a046a

Source dataset

uspto-grants-2005_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06900216B2