Boron tribromide dichloromethane → [2-(3-Bromo-benzyl)-4,5-dimethyl-furan-3-yl]-(3,5-diisopropyl-4-hydroxy-phenyl)-methanone

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Reaction Steps

The title compound was prepared according to the procedure in Example 5, step 3 using [2-(3-bromo-benzyl)-4,5-dimethyl-furan-3-yl]-(3,5-diisopropyl-4-methoxy-phenyl)-methanone (1.34 g, 2.78 mmol) and 1M boron tribromide/CH2Cl2 (5.84 mL) in CH2Cl2. Purification on Biotage KP-Sil eluting with 15% acetonelhexane gave 0.995 g (73%) of the title compound. 1H NMR (DMSO-d6) δ1.14 (d, 12 H), 1.80 (s, 3 H), 2.19 (s, 3 H), 3.32 (septet, 2 H), 3.87 (s, 2 H), 7.09 (d, 1 H), 7.22 (t, 1 H), 7.26 (s, 1H), 7.39 (d, 1 H), 7.43 (s, 2 H), 9.13 (s, 1 H). IR (KBr) 3350, 2950, 1580, 1560 and 1325 cm−1. mass spectrum (EI) m/z 468 (M+). Anal. Calcd. for C26H29BrO3: C, 66.53; H, 6.23; N, 0.00. Found: C, 66.50; H, 6.22; N, 0.08.

Provenance & Evidence