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

HRID 433830Notes

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, 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) δ8.01-7.38 (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, 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-c76a58fe068b403187a525cd59ef5bcd
Source dataset: uspto-grants-2003_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06668527B2

Reaction notes

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