Hydrochloric Acid → 4-(Bromomethyl)benzaldehyde

Participants

Reaction Steps

To a THF-toluene (2.4 L -0.24 L) solution of α bromo p tolunitrile (266.4 g, 1.36 mol) maintained at an internal temperature below 0° C. was added DIBAL-H in hexane (1.0 M) (1.49 L, 1.49 mol) over a period of 2 h. After a period of 1.5 h, the reaction mixture was transferred via canula to a 3N HCl solution (8 L) at 0° C. To the resulting suspension EtOAc (4 L) and THF (0.8 L) were added. After stirring, the organic phase was separated and evaporated to give a yellow solid. The solid was stirred, in 20% EtOAc in hexane (1.3 L) for 3 hours. After filtration and drying, the title compound was obtained (210 g).

Provenance & Evidence