Sodium Bicarbonate → 6-bromo-2H-chromene

Participants

Reaction Conditions

Reaction Steps

To a solution of 6-bromochroman-4-ol (3.98 kg, 17.4 mol) in toluene (18 L) add p-toluenesulfonic acid monohydrate (95 g, 499.42 mmol) at room temperature. Attach a Dean-Stark trap and reflux for 3 hr. and 50 min. Allow the mixture to cool to 50° C. in air and pour into saturated aqueous sodium bicarbonate (10 L) and ice (about 3 kg) with stirring. Separate the two layers. Back extract the aqueous layer with methyl tert-butyl ether (4 L). Wash the organic layer with saturated sodium bicarbonate (10 L) and brine (1×10 L), and evaporate the solvent under reduced pressure to obtain the title compound as a brown oil (4.90 kg, >100%, contains toluene). LCMS m/z (79Br) 209 [M+H]+.

Provenance & Evidence