Yield:-

Reaction Conditions:

with triphenylphosphine;diethylazodicarboxylate in tetrahydrofuran at 0 - 16; for 16 h;Mitsunobu reaction;

Steps:

37.a

A solution of diethyl azodicarboxylate (0.75 mL, 4.4 mmol) in dry THF (10 mL) was added slowly to a solution of Ph₃P (1.15 g, 4.45 mmol), vanillin (0.61 g, 4.0 mmol) and 2-chloro-4-fluorobenzyl alcohol (0.64 g, 4.0 mmol) in THF (15 mL) at 0° C. under argon. After the addition was complete, the mixture was slowly warmed to rt and stirred for 16 h. The mixture was concentrated and the residue purified by flash chromatography. Elution with 10% acetone in CH₂Cl₂ yielded 4-(2-chloro-4-fluoro-benzyloxy)-3-methoxy-benzaldehyde as colorless solid.

References:

US2006/14812,2006,A1 Location in patent:Page/Page column 20