Reaktion #67280

Reaktionsgleichung

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

sodium methanesulfinate

L-proline

K2CO3

→

title compound

Ausbeute 33.2%

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

Ausbeute 33.2%

Lösungsmittel

DMSO

Reaktionsbedingungen

Aufarbeitung

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

Vorschrift

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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