Hydrogen Bromide → 2-Bromo-3-bromomethyl-1,4-dimethoxynaphthalene

Participants

Reaction Steps

Alcohol 26 (9.80 g, 45.0 mmol) was dissolved in CH2Cl2 (150.0 mL) in a flame-dried 500 mL round bottom flask. Concentrated HBr (22.0 mL) was added to displace the alcohol, the solution was stirred for 2 h at room temperature. The reaction was then diluted with CH2Cl2 (300.0 mL) and Br2 (2.40 mL, 47.7 mmol) was added dropwise dissolved in CH2Cl2 (50.0 mL) at room temperature. The reaction was stirred for 6 hours further before being washed with brine, dried over MgSO4, and filtered. The resulting solid was purified using flash column chromatography (1:19 EtOAc:hexanes) to provide 36 (9.02 g, 25.1 mmol, 56%) as a yellow powder.

Provenance & Evidence