2-Bromo-3-methylthiophene → HCID 68842710, compound

Participants

Reaction Steps

To a −78° C. solution of 2-bromo-3-methyl-thiophene (2.0 g, 17.75 mmol) and THF (30 mL) is added 2.0 M LDA (9.32 mL, 18.63 mmol). After 30 minutes at −78° C. tetrahydro-pyran-4-one (2.3 mL, 23.07 mmol) is added and the solution is warmed to ambient temperature. The solution is washed with sat. NH4Cl (30 mL). The aqueous phases is extracted with EtOAc. The combined organic layers are dried over MgSO4, filtered and concentrated. The residue is purified by ISCO column chromatography (30%-100% EtOAc/hexane gradient) furnish the title compound (2.3 g, 8.30 mmol, 47%). 1H NMR (CDCl3), δ 1.82 (m, 2H), 2.00 (s, 3H), 2.06-2.15 (m, 3H), 2.16 (s, 3H), 3.77-3.84 (m, 2H), 3.87 dt, J=11.3, 2.2 Hz, 2H), 6.67 (s, 1H). LC/MS (m/z): calcd. for C10H13BrO2S (M+H)+: 277.0; found: 260.9.

Provenance & Evidence