1,3-Dibromopropane → HCID 18439648, compound

Participants

Reaction Steps

A solution of (2S)-N-(4-hydroxy-5-methoxy-2-nitrobenzoyl)-4-fluoro pyrrolidine 2-carboxaldehyde diethylthioacetal VI (418 mg, 1 mmol), 1,3-dibromopropane (101 mg, 0.5 mmol) and K2CO3 (414 mg, 3 mmol) in dry acetone (40 ml) was refluxed for 48 h. After the completion of reaction as indicated by TLC, EtOAc-hexane (7:3), the reaction mixture was poured on to the water and then extracted with ethylacetate. Evaporation of the organic layer gave the crude product, which was further purified by column chromatography on silica gel eluting with EtOAc-hexane (1:1) to give the pure 1,1′-{[(Propane-1,3 diyl)dioxy]bis[2-nitro-5-methoxy-1,4-phenylene)carbonyl]}bis[4-fluoro pyrrolidine-2-carboxaldehyde diethylthioacetal] VII. H1 NMR (CDCl3, 200 MHz): δ 1.2–1.39 (m, 12H), 2.4–2.68 (m, 6H), 2.7–2.9 (m, 8H), 3.41–3.62 (m, 4H), 3.99 (s, 6H), 4.29–4.4 (m, 4H), 4.52 (d, j=3.9 Hz, 2H), 4.69–4.79 (m, 2H), 5.05 (t, 1H), 6.85 (s, 2H), 7.63 (s, 2H). FAB MASS: 877 (M+H)

Provenance & Evidence