4-(3-fluoro-benzyloxy)-benzaldehyde synthesis

5synthesis methods

Product Name:4-(3-fluoro-benzyloxy)-benzaldehyde
CAS Number:66742-57-2
Molecular formula:C14H11FO2
Molecular Weight:230.23

4-(3-fluoro-benzyloxy)-benzaldehyde is synthesized by the reaction of 4-Hydroxybenzaldehyde with 3-fluorobenzyl bromide. 4-Hydroxybenzaldehyde, 3-fluorobenzyl bromide, potassium carbonate, and acetone were sequentially added to a single-neck round bottom flask. Reaction at 60 ° C for 5 h. Cool to room temperature, filter, and collect the filtrate.Purification by direct column chromatography. 4-(3-fluoro-benzyloxy)-benzaldehyde was obtained as a white solid (1.78 g, 94.4%).

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Yield:66742-57-2 97.5%

Reaction Conditions:

with potassium carbonate;cetyltrimethylammonium bromide in toluene; for 7 h;Product distribution / selectivity;Heating / reflux;

Steps:

11.3

4-(3-Fluorobenzyloxy)benzaldehyde is prepared in 97.5% yield with a content of 3- (3-fluorobenzyl) -4- (3-fluorobenzyloxy)benzaldehyde (Via) of 0.45% by weight, determined by GC (see Example 24B), by reacting 4- hydroxybenzaldehyde (15.6g) with 3-fluorobenzyl methanesulfonate instead of 3-fluorobenzyl chloride according to the same procedure of Example 11. This product is further purified according to the procedure of the Example 11.1 to lower the content of impurity (Via) to 0.01 % by weight.

References:

WO2009/74478,2009,A1 Location in patent:Page/Page column 60

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456-42-8 Synthesis