Réaction #67280

Équation de réaction

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

sodium methanesulfinate

L-proline

K2CO3

→

title compound

Rendement 33.2%

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

Rendement 33.2%

Solvants

DMSO

Conditions de réaction

Traitement

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

Mode opératoire

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).

Source