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

HRID 433676Notes

Reaction equation

[CH3:1][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>[CH3:1][O:2][C:3](=[O:19])[CH2:4][C:5]1[CH:10]=[CH:9][C:8]([C:22]2[CH:21]=[CH:20][C:29]3[C:24](=[CH:25][CH:26]=[CH:27][CH:28]=3)[CH:23]=2)=[CH:7][CH:6]=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, 1 M 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)

Workup

customThe reaction was flushed with nitrogen
additionThe reaction was then diluted with ethyl acetate
extractionextracted with water, 1 M 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-03c02192e5834de9a67d3a1692bd516c
Source dataset: uspto-grants-2003_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06667331B2

Reaction notes

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