Cesium fluoride → 2-(4-(Naphthalen-2-yl)phenyl)acetic acid

HRID 1071285Notes

Reaction equation

C[O:2][C:3](=[O:19])[CH2:4][C:5]1[CH:10]=[CH:9][C:8](OS(C(F)(F)F)(=O)=O)=[CH:7][CH:6]=1.[CH:20]1[C:29]2[C:24](=[CH:25][CH:26]=[CH:27][CH:28]=2)[CH:23]=[CH:22][C:21]=1B(O)O.[F-].[Cs+]>C(COC)OC>[CH:28]1[C:29]2[C:24](=[CH:23][CH:22]=[CH:21][CH:20]=2)[CH:25]=[CH:26][C:27]=1[C:8]1[CH:9]=[CH:10][C:5]([CH2:4][C:3]([OH:2])=[O:19])=[CH:6][CH:7]=1

Participants

Conditions

Temperature: 100 °C

Procedure

Tetrakis triphenyphosphine palladium (65 mg, 7.4 mol %) was added to a dimethoxy ethane (5.4 mL) solution of (4-Trifluoromethanesulfonyloxy-phenyl)-acetic acid methyl ester (447 mg, 1.5 mmol), 2-naphthaleneboronic acid (286 mg, 1.67 mmol) and cesium fluoride (505 mg, 3.33 mmol). The reaction was flushed with nitrogen and heated in an oil bath to 100° C. while stirring for 3 hours. The reaction was then diluted with ethyl acetate and extracted with water, 1M sodium hydroxide, water and brine. The organic portion was dried over magnesium sulfate and concentrated in vacuo. The resulting residue was chromatographed on a Biotage Flash 40S column eluting with 5% ethyl acetate in hexanes to give the title compound as a clear oil (273 mg, 66%). 1H NMR (400 MHz, CDCl3) δ 8.01-7.38 (m, 11H), 3.72 (s, 3H), 3.69 (2H) E. (4-Trifluoromethanesulfonyloxy-phenyl)-acetic acid methyl ester

Workup

customThe reaction was flushed with nitrogen
additionThe reaction was then diluted with ethyl acetate
extractionextracted with water, 1M sodium hydroxide, water and brine
dry with materialThe organic portion was dried over magnesium sulfate
concentrationconcentrated in vacuo
customThe resulting residue was chromatographed on a Biotage Flash 40S column
washeluting with 5% ethyl acetate in hexanes

Sources & evidence

ORD record: ord-cbe96393996e4f21a2f71af36518acef
Source dataset: uspto-grants-2005_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06903128B2

Reaction notes

Loading…