反应详情

温度

80 °C

A mixture of ethyl 2-[4-chloro-3-fluoro-2-iodo-6-(2-methyl-1,3-dioxolan-2-yl)phenoxy]propanoate (1.83 g, 3.99 mmol), 4,4,5,5-tetramethyl-2-vinyl-1,3,2-dioxaborolane (0.880 mL, 5.19 mmol), and potassium carbonate (1.65 g, 12.0 mmol) in 1,4-dioxane (15.6 mL) and water (7.8 mL) was degassed with nitrogen for 10 min. The reaction mixture was treated with [1,1′-bis(diphenylphosphino)ferrocene]dichloropalladium(II) complex with dichloromethane (1:1) (163 mg, 0.199 mmol), degassed with nitrogen for another 10 min, and heated at 80° C. for 2 h. The reaction mixture was filtered through Celite and washed with ethyl acetate. The filtrate was poured into water. The aqueous layer was separated and re-extracted with ethyl acetate. The combined organic extracts were washed with brine, dried over sodium sulfate, filtered, and concentrated give a crude residue. Purification by flash column chromatography (100% hexanes to 15% EtOAc/hexanes) gave the desired product (2.25 g, 57%) as a mixture of enantiomers. LCMS calculated for C17H21ClFO5 (M+H)+: m/z=359.1; found: 359.1.

1. customwas degassed with nitrogen for 10 min
2. customdegassed with nitrogen for another 10 min
3. filtrationThe reaction mixture was filtered through Celite
4. washwashed with ethyl acetate
5. additionThe filtrate was poured into water
6. customThe aqueous layer was separated
7. extractionre-extracted with ethyl acetate
8. washThe combined organic extracts were washed with brine
9. dry with materialdried over sodium sulfate
10. filtrationfiltered
11. concentrationconcentrated
12. customgive a crude residue
13. customPurification by flash column chromatography (100% hexanes to 15% EtOAc/hexanes)