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0 °C

Dissolve 5-(4-chloro-phenyl)-3-vinyl-thiophene-2-carboxylic acid methyl ester (5.35 g, 19.19 mmol) in tetrahydrofuran (220 mL) and cool to 0° C. Slowly add 9-borabicyclo[3.3.1]nonane (112 mL, 0.5 M, 56 mmol), warm the reaction to room temperature with stirring for 16 h. Cool the mixture to 0° C. and slowly add hydrogen peroxide (74 mL, 721 mmol) followed by 5 N sodium hydroxide (74 mL, 370 mmol). Add water (14 mL) and extract with ethyl acetate (3×150 mL). Dry the solution over Na2SO4, filter and evaporate. Purify by chromatography eluting with 50% ethyl acetate/hexane to afford 5.70 g (100%) of the title compound. LC-MS/ES m/z (35Cl) 296.7.0 [M+H]+.

1. customthe reaction to room temperature
2. temperatureCool the mixture to 0° C.
3. extractionAdd water (14 mL) and extract with ethyl acetate (3×150 mL)
4. dry with materialDry the solution over Na2SO4
5. filtrationfilter
6. customevaporate
7. customPurify by chromatography
8. washeluting with 50% ethyl acetate/hexane