Реакция #67280

Уравнение реакции

(7-bromo-5-fluoro-2,3-dihydro-1,4-benzodioxin-2-yl)methanol

sodium methanesulfinate

L-proline

K2CO3

→

title compound

Выход 33.2%

[5-FLUORO-7-(METHYLSULFONYL)-2,3-DIHYDRO-1,4-BENZODIOXIN-2-YL]METHANOL

Выход 33.2%

Растворители

DMSO

Условия реакции

Обработка

1. 1
   Другоеflushed vials
2. 2
   ТемператураAfter cooling to ambient temperature
3. 3
   workup.ADDITIONthe batches were mixed
4. 4
   workup.ADDITIONwater and EtOAc were added
5. 5
   Экстракцияthe water phase was extracted with EtOAc
6. 6
   ПромывкаThe combined organic phases were washed with LiCl (5%), HCl (1 N), brine
7. 7
   Сушкаdried (Na2SO4)
8. 8
   Другоеevaporated to dryness
9. 9
   workup.ADDITIONThe product was mixed with another batch of the same compound
10. 10
    ДругоеPurification on flash column chromatography (isooctane/EtOAc/MeOH)

Методика

A mixture of (7-bromo-5-fluoro-2,3-dihydro-1,4-benzodioxin-2-yl)methanol (0.6 g, 2.3 mmol), sodium methanesulfinate (85%) (0.4 g, 3.5 mmol), CuI (0.04 g, 0.2 mmol), L-proline (0.05 g, 0.5 mmol) and K2CO3 (0.06 g, 0.5 mmol) in DMSO (6 ml) was heated in two batches under microwave radiation at 140° C. for 2 h in nitrogen-flushed vials. After cooling to ambient temperature, the batches were mixed, water and EtOAc were added and the water phase was extracted with EtOAc. The combined organic phases were washed with LiCl (5%), HCl (1 N), brine, dried (Na2SO4) and evaporated to dryness. The product was mixed with another batch of the same compound. Purification on flash column chromatography (isooctane/EtOAc/MeOH) gave the title compound (0.2 g). MS m/z (rel. intensity, 70 eV) 262 (M+, bp), 231 (32), 206 (12), 183 (17), 152 (14).

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