Hydrochloric Acid → HCID 118006008, compound

Participants

Reaction Steps

1.0 M diisobutylaluminium hydride in toluene (11.5 mL) was slowly added to a solution of 30 (1.3 g, 4.6 mmol) in THF (15 mL) at −78° C. After the addition was completed, the mixture was allowed to warm to room temperature and continuously stirred for 18 h. The mixture was poured in to HCl aqueous solution (0.5 N, 50 mL) and extracted in ethyl acetate (2×100 mL). The combined organic layer was dried over anhydrous Na2SO4, filtered, concentrated rotary evaporation, and purified by column chromatography to give (5-bromo-7-fluoronaphthalen-2-yl)methanol (31) (98%). 1H NMR (400 MHz, CDCl3) δ 8.19 (d, J=8.8 Hz, 1H), 7.77 (s, 1H), 7.59 (d, J=8.2 Hz, 1H), 7.53 (d, J=9.0 Hz, 1H), 7.45 (d, J=11.4 Hz, 1H), 4.90 (s, 2H). GC-MS (ES) for C11H8BrFO [M+1]+ 255.

Provenance & Evidence