تفاعل #67280

معادلة التفاعل

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

sodium methanesulfinate

L-proline

K2CO3

→

title compound

المردود 33.2%

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

المردود 33.2%

المذيبات

DMSO

ظروف التفاعل

المعالجة

1. 1
   أخرىflushed vials
2. 2
   درجة الحرارةAfter cooling to ambient temperature
3. 3
   workup.ADDITIONthe batches were mixed
4. 4
   workup.ADDITIONwater and EtOAc were added
5. 5
   استخلاصthe water phase was extracted with EtOAc
6. 6
   غسيلThe combined organic phases were washed with LiCl (5%), HCl (1 N), brine
7. 7
   تجفيفdried (Na2SO4)
8. 8
   أخرىevaporated to dryness
9. 9
   workup.ADDITIONThe product was mixed with another batch of the same compound
10. 10
    أخرىPurification on flash column chromatography (isooctane/EtOAc/MeOH)

الإجراء التجريبي

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).

المصدر