Boron trifluoride etherate → HCID 86682286, compound

Participants

Reaction Conditions

Reaction Steps

To a 250 mL RBF were added 4-(3-bromo-4-methoxyphenyl)hepta-1,6-dien-4-ol (4.85 g, 16.32 mmol), triethylsilane (5.21 mL, 32.6 mmol), and CH2Cl2 (50 mL). The flask was flushed with N2. BF3.Et2O (2.275 mL, 17.95 mmol) was added via syringe at −78° C. The resulting reaction mixture was stirred at −78° C. for 1 hr and was then allowed to warm to 0° C. briefly. 50 mL 10% KOH was added at 0° C. and the reaction mixture was extracted with 50 mL EtOAc/Hexane (1:1). The organics were washed with 30 mL brine, dried over sodium sulfate, filtered and concentrated. Crude product was purified by silica gel chromatography, eluted with 10% EtOAc/Hexane to give 2-bromo-4-(hepta-1,6-dien-4-yl)-1-methoxybenzene (3.6 g) as colorless oil. 1H NMR (500 MHz, CDCl3:) δ 7.38 (s, 1H), 7.06 (d, 1H), 6.85 (d, 1H), 5.66 (m, 2H), 4.99 (d, 4H), 3.91 (s, 3H), 2.66 (m, 1H), 2.42 (m, 2H), 2.33 (m, 2H).

Provenance & Evidence