Boron tribromide → 3-Chloro-4-methoxysalicylaldehyde

Participants

Reaction Conditions

Reaction Steps

To a solution of 72.0 g. (0.359 mol) of (13h) in 450 ml. of CH2Cl2 at -50° C. under N2 was added dropwise 90.0 g. (0.359 mol) of BBr3. After the addition was complete, the reaction mixture was warmed to 0° C. and stirred for 1 hour. The reaction mixture was then poured into 500 ml. of ice-water and extracted with EtOAc. The organic solution was washed with aqueous NaCl and dried over Na2SO4. Evaporation of the EtOAc gave a residue that was rapidly passed through a silica gel column eluting with an EtOAc/CH2Cl2 mixture. This afforded 49.5 g. of (14h), m.p. 114°-117° C. Analysis (C8H7ClO3) C,H.

Provenance & Evidence