反应详情

温度

-78 °C

To a solution of oxalyl chloride 2M in dichloromethane (DCM) (11 m1, 22 mmol, 2.2 molar equivalents) cooled to −78° C., was added dropwise a solution of dimethylsulfoxyde (DMSO) (3.10 ml, 44 mmol, 4.4 molar equivalents) in DCM (10 ml). The solution was then stirred at −78° C. for 5 minutes and 3-fluorobenzene-1,2-dimethanol (Compound 17) (1.55 g, 10 mmol, 1.0 molar equivalent) dissolved in a mixture of DCM-DMSO (1-2 ml) added dropwise. The solution was then stirred for 1 hour at −78° C. and triethylamine (25 ml) was slowly added at −78° C. The reaction mixture was then stirred for 10 minutes at −78° C. and slowly warmed up to room temperature. Ice-cold water (50 ml) was added to the reaction. mixture and the aqueous layer extracted with DCM (3 times 50 mls). The organic fractions A were combined, dried over magnesium sulfate, filtered and concentrated in vacuum to give a brown oil. Purification by distillation gave the title compound as a light yellow solid (1.10 g, 73%) 1H NMR (300.13 MHz, CDCl3) δ(ppm) 7.36-7.50 (m, 1H) 7.69-7.79 (m, 2H) 10.51 (s, 1H) 10.57 (s, 1H). 19F NMR (282.38 MHz, CDCl3) δ(ppm) −118.90 (s).

1. additionadded dropwise
2. stirringThe solution was then stirred for 1 hour at −78° C.
3. stirringThe reaction mixture was then stirred for 10 minutes at −78° C.
4. temperatureslowly warmed up to room temperature
5. extractionmixture and the aqueous layer extracted with DCM (3 times 50 mls)
6. dry with materialdried over magnesium sulfate
7. filtrationfiltered
8. concentrationconcentrated in vacuum
9. customto give a brown oil
10. customPurification
11. distillationby distillation