반응 #676281

반응 방정식

(3-methylisoxazol-5-yl)methyl benzoate

N-bromosuccinimide

→

desired product

수율 79.0%

(4-Bromo-3-methylisoxazol-5-yl)methyl benzoate

수율 79.0%

용매

brine

acetic acid

반응 조건

후처리

1. 1
   추출extracted with ethyl acetate
2. 2
   기타The organic layer was separated
3. 3
   세척washed with brine
4. 4
   건조dried over magnesium sulfate
5. 5
   여과filtered
6. 6
   농축concentrated
7. 7
   기타to give the crude product
8. 8
   기타Purification by flash column chromatography (100% hexanes to 20% ethyl acetate/hexanes)

실험 절차

A solution of (3-methylisoxazol-5-yl)methyl benzoate (20.1 g, 92.4 mmol) in acetic acid (77.3 mL) was treated with N-bromosuccinimide (19.7 g, 111 mmol) and heated in a sealed tube at 90° C. for 4 h. The reaction mixture was diluted with brine and extracted with ethyl acetate. The organic layer was separated, washed with brine, dried over magnesium sulfate, filtered, and concentrated to give the crude product. Purification by flash column chromatography (100% hexanes to 20% ethyl acetate/hexanes) gave the desired product (21.6 g, 79%). LCMS calculated for C12H11BrNO3 (M+H)+: m/z=296.0, 298.0. found: 296.0, 298.0.

출처