4-Hydroxybenzaldehyde → 3-Bromo-4-hydroxybenzaldehyde

Participants

Reaction Conditions

Reaction Steps

To a solution of 4-hydroxybenzaldehyde (10.00 g, 82 mmol) in chloroform (170 mL) was added bromine (13.76 g, 86.1 mmol) dropwise as a solution in chloroform (80 mL). Upon completion of addition, the reaction was stirred for 30 mins. at room temperature then warmed to 40° C. for 1 hr. The reaction was diluted with aqu. sat'd NaHCO3 (250 mL) and the layers were separated. The aqueous was extracted with CH2Cl2 (2×250 mL). The organics were combined, dried with MgSO4 and concentrated to afford 7.49 g of 3-bromo-4-hydroxybenzaldehyde which contains 10% of 3,5-dibromo-4-hydroxybenzaldehyde.

Provenance & Evidence