Bromine → HCID 24831456, compound

Participants

Reaction Steps

To a stirred solution of Example 2 (0.83 g, 3.50 mmol) in THF (50 mL) at 0° C. was added, dropwise, Br2 (0.56 g, 3.50 mmol) and the reaction mixture was stirred for 20 minutes. The reaction mixture was then poured into brine (200 mL) and extracted with EtOAc (3×100 mL). The combined organics were dried over MgSO4, filtered and concentrated in vacuo. Purification by column chromatography (SiO2, 1:5 EtOAc/hexanes) gave the title compound as a pale brown solid (0.79 g, 72%). δH (DMSO-d6) 3.77-3.74 (4H, m), 3.22-3.18 (4H, m), 2.70-2.67 (2H, m), 2.52-2.47 (2H, m), 2.10-2.04 (2H, m). δ 13C (DMSO-d6) 189.7, 160.2, 152.7, 124.6, 97.4, 65.9 (2×CH2), 51.9 (2×CH2), 37.3, 25.9, 23.4. LCMS (ES+) 315.0 and 317.0 (M+H)+.

Provenance & Evidence