Bromine → HCID 68863959, compound

Participants

Reaction Steps

A mixture of Example 362A (1.05 g, 4.79 mmol) in 4:1 ethanol/water (20 mL) was reduced with iron (1.1 g) in the presence of ammonium chloride (0.12 g) using the procedure described in Example 275A. The crude product (0.91 g, 4.79 mmol) was treated with bromine (0.245 mL, 4.79 mmol) in 9 mL of chloroform and 0.9 mL of N,N-dimethylformamide following the procedure described in Example 275B. The obtained hydrobromide salt was treated with 10% sodium hydrogen carbonate in ethyl acetate. The ethyl acetate layer was washed with brine (4×), dried (Na2SO4), filtered, and concentrated. The residue was purified by silica gel column chromatography eluting with 10% ethyl acetate in n-hexane to provide 730 mg of the desired product. MS (ESI(−)) m/e 266 (M−H)−; 1H NMR (300 MHz, DMSO-d6) δ 6.97 (m, 2H), 5.39 (m, 2H), 2.80 (t, 2H), 1.84 (t, 2H), 1.10 (s, 6H).

Provenance & Evidence