4-(benzyloxy)-3-fluorobenzoic acid synthesis

5synthesis methods

Product Name:4-(benzyloxy)-3-fluorobenzoic acid
CAS Number:152552-64-2
Molecular formula:C14H11FO3
Molecular Weight:246.23

Benzoic acid, 3-fluoro-4-(phenylmethoxy)-, phenylmethyl ester

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152552-64-2
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Yield:152552-64-2 90%

Reaction Conditions:

Stage #1: benzyl-4-(benzyloxy)-3-fluorobenzoatewith lithium hydroxide monohydrate;sodium hydroxide in tetrahydrofuran;methanol; for 18 h;
Stage #2: with hydrogenchloride in tetrahydrofuran;methanol;lithium hydroxide monohydrate; pH=3;Cooling with ice;

Steps:

31A.B

Benzyl 4-(benzyloxy)-3-fluorobenzoate (1 1.6 g, 34.2 mmol) was dissolved intetrahydrofuran (50 ml.) and methanol (50 ml_). Aqueous sodium hydroxide (70 ml_, 1 M) was added to the reaction mixture and stirred for 18 hours. The reaction was cooled in an ice bath and acidified to pH 3 by careful addition of aqueous 1 Ab solution of hydrochloric acid. A white solid precipitated out and was filtered and dried over night to give the desired product, 4-(benzyloxy)-3-fluorobenzoic acid, as a white solid (7.6 g, 90%). 1 H NMR (500 MHz, deuterodimethylsulfoxide) delta ppm 3.32 (br. s., 1 H) 5.27 (s, 2 H) 7.34 - 7.39 (m, 2 H) 7.42 (t, J=7.44 Hz, 2 H) 7.45 - 7.50 (m, 2 H) 7.68 (dd, J=1 1 .83, 2.07 Hz, 1 H) 7.75 (d, J=8.78 Hz, 1 H)

References:

WO2012/69948,2012,A1 Location in patent:Page/Page column 71-72

350-29-8 Synthesis