Sodium Hydroxide → 5-Fluoro-2-(pyrimidin-2-yl)benzoic acid

HRID 243835

Reaction equation

C[O:2][C:3](=[O:17])[C:4]1[CH:9]=[C:8]([F:10])[CH:7]=[CH:6][C:5]=1[C:11]1[N:16]=[CH:15][CH:14]=[CH:13][N:12]=1.[OH-].[Na+]>O>[F:10][C:8]1[CH:7]=[CH:6][C:5]([C:11]2[N:12]=[CH:13][CH:14]=[CH:15][N:16]=2)=[C:4]([CH:9]=1)[C:3]([OH:17])=[O:2]

Participants

Conditions

Temperature: 72 °C

Procedure

To a solution of 5-fluoro-2-pyrimidin-2-ylbenzoic acid methyl ester (1.72 g, 7.407 mmol) in 2-methyl-THF (20 mL) was added sodium hydroxide (0.74 g, 18.517 mmol) and water (20 mL). The mixture was heated to 72° C. and stirred for 2 h. The layers were separated and the aqueous layer was extracted with additional MTBE. A 50% HCl(aq) solution was then dripped into the aqueous layer until a pH of 1 was reached. The resulting solids were filtered to provide the desired product as an off-white solid (1.34 g, 83% yield). 1H NMR (400 MHz, CD3OD): 8.82 (d, J=5.0 Hz, 2H), 7.89 (dd, J=8.6, 5.4 Hz, 1H), 7.53 (dd, J=9.0, 2.7 Hz, 1H), 7.39 (m, 2H).

Workup

customThe layers were separated
extractionthe aqueous layer was extracted with additional MTBE
filtrationThe resulting solids were filtered

Sources & evidence

ORD record: ord-7138cbed998c4c148de20154b57b26df
Source dataset: uspto-grants-2014_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08653263B2

Linked notes

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