2,6-Dimethoxyphenol → 4-Bromo-2,6-dimethoxyphenol

Participants

Reaction Conditions

Reaction Steps

To a cooled (−78° C.) solution of 2,6-dimetoxyphenol (13)(15 g, 97.35 mmol) in CH2Cl2 (200 ml) was added N-bromosuccinimide (17.4 g, 97.35 mmol) portionwise over twenty minutes. The reaction mixture was stirred at −78° C. under an inert atmosphere for four hours before being allowed to warm to room temperature where it was stirred for a further 16 hours. The solvent was then removed in vacuo to give a slurry that was purified by flash chromatography (SiO2) (7:3—CH2Cl2:Hexanes) and then re-crystallised from CH3Cl/hexanes to give the title compound as a white solid that was analytically clean (9.66 g, 42.57%). m/z (LC-MS, ESP): 231 [M−H]−, R/T=3.17 mins

Provenance & Evidence