3-CHLORO-4-FLUOROBENZYL ALCOHOL synthesis

Yield:-

Reaction Conditions:

with sodium tetrahydroborate in tetrahydrofuran;methanol at 0; for 0.0333333 h;

Steps:

A
[00202] A solution of 3-chloro-4-fluorobenzaldehyde (3 g) in THF (40 ml) was added over 2 minutes to a stirred suspension of sodium borohydride (1.07 g) in methanol (40 ml) at 0° C. The mixture was allowed to warm to room temperature and then quenched with water. The resulting suspension was partitioned between water and diethyl ether and the combined organic extracts were dried and concentrated in vacuo. The residue was dissolved in dichloromethane (90 ml) and triphenylphosphine (4.62 g) and tetrabromomethane (6.64 g) were added at 0° C. The mixture was allowed to warm to room temperature overnight then concentrated in vacuo and the residue purified by column chromatography using iso-hexane as eluent to yield the desired product (3.57 g, 85%). NMR: δ 4.7 (s, 2H), 7.4 (m, 2H), 7.7 (m, 1H).

References:

AstraZeneca AB US6737435, 2004, B1 Location in patent:Page/Page column 17-18