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299181-56-9

Benzoic acid, 4-fluoro-3-(4-morpholinylsulfonyl)- synthesis

4synthesis methods
Benzoic acid, 4-fluoro-3-(4-morpholinylsulfonyl)-, methyl ester

299181-55-8
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Benzoic acid, 4-fluoro-3-(4-morpholinylsulfonyl)-

299181-56-9
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Yield:299181-56-9 88%

Reaction Conditions:

with lithium hydroxide in methanol;water;

Steps:

6 4-Fluoro-3-(morpholine-4-sulfonyl)-benzoic Acid

EXAMPLE 6 4-Fluoro-3-(morpholine-4-sulfonyl)-benzoic Acid A solution of lithium hydroxide (1.56 g, 37.3 mmol) in water (5 mL) was added to a stirred solution of 4-fluoro-3-(morpholine-4-sulfonyl)-benzoic acid, methyl ester (Example 5, 2.26 g, 7.45 mmol) in methanol (50 mL) / water (10 mL) at 0° C. After 4 hours, the clear solution was quenched with aqueous hydrochloric acid (2M, 10 mL). Concentration in vacuo to remove the methanol afforded a white precipitate. Filtration and drying afforded the title compound as a white powder (1.89 g, 88% yield): 1H-NMR (CDCl3) δ3.21 (td, J=7, 1.5 Hz, 4H), 3.75 (td,, J=7, 1.5 Hz, 4H), 3.98 (s, 3H), 7.28 (dd, J=18, 15 Hz, 1H), 8.28 (ddd, J=7, 5, 2 Hz, 1H), 8.51 (dd, J=7, 2 Hz, 1H): MS (ESI) [M-H]-at m/z 303.

References:

US6355633,2002,B1