3-Hydroxybenzaldehyde → 2-Bromo-5-hydroxybenzaldehyde

Participants

Reaction Conditions

Reaction Steps

3-Hydroxybenzaldehyde (120 g, 0.98 moles) was suspended in 2400 mL of CH2Cl2 in a 5 L 4-neck round bottom flask equipped with overhead stirrer, temperature probe, addition funnel, and condenser. The mixture was heated to 35-40° C. in order to dissolve the starting material. Bromine (52 mL, 1.0 moles, 1.02 eq.) was added dropwise through the addition funnel at a rate which maintained the reaction temperature between 35-38° C. The mixture was then allowed to stir overnight at 35° C. The mixture was slowly cooled to −5-0° C. over two hours and then allowed to stir at that temperature for 1 h more. The solid which formed was then collected by filtration through a Buchner funnel and the filter cake washed with 400 mL of a cold 1:1 CH2Cl2:heptane solution. The gray solid was then dried in vacuo (0.2 mm Hg) at room temperature. Yield=124.3 g (63%).

Provenance & Evidence