Lithium hydroxide, monohydrate → 2-(4-Cyano-2-fluoro-phenoxymethyl)-benzoic acid

HRID 1875772Notes

Reaction equation

C[O:2][C:3](=[O:21])[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[CH2:10][O:11][C:12]1[CH:17]=[CH:16][C:15]([C:18]#[N:19])=[CH:14][C:13]=1[F:20].O.[OH-].[Li+]>O1CCCC1.O>[C:18]([C:15]1[CH:16]=[CH:17][C:12]([O:11][CH2:10][C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[C:3]([OH:21])=[O:2])=[C:13]([F:20])[CH:14]=1)#[N:19]

Participants

Conditions

Temperature: 25 °C

Procedure

To a solution of 2-(4-cyano-2-fluoro-phenoxymethyl)-benzoic acid methyl ester (2.17 g, 7.6 mmol) in tetrahydrofuran (30 ml) was added a solution of lithium hydroxide monohydrate (1.59 g, 38.03 mmol) in water (30 ml) and the resulting mixture was allowed to stir at 25° C. for 12 h. The solvent was removed in vacuo, the residue was diluted with water (20 ml), washed with diethyl ether (2×15 ml). The aqueous layer was then acidified to pH 5 with 2N aqueous hydrochloric acid and extracted with ethyl acetate (2×40 ml). The combined organic layers were washed with water (2×25 ml), brine, dried over sodium sulfate, filtered, and evaporated to afford the desired compound as a colorless solid (90%). MS (Turbo Spray): m/z=272.1 (M+H).

Workup

customThe solvent was removed in vacuo
additionthe residue was diluted with water (20 ml)
washwashed with diethyl ether (2×15 ml)
extractionextracted with ethyl acetate (2×40 ml)
washThe combined organic layers were washed with water (2×25 ml), brine
dry with materialdried over sodium sulfate
filtrationfiltered
customevaporated

Sources & evidence

ORD record: ord-543608502ea44e119043fff0f993a301
Source dataset: uspto-grants-2012_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08309581B2

Reaction notes

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