反应 #2286319

反应方程式

methyl 3,5-dibromo-4-methylbenzoate

N-bromosuccinamide

2,2′-azobisisobutyronitrile

→

3,5-dibromo-4-bromomethyl-benzoic acid methyl ester

收率 99.0%

3,5-Dibromo-4-bromomethyl-benzoic acid methyl ester

收率 99.0%

溶剂

carbon tetrachloride

反应条件

后处理

1. 1
   温度The reaction mixture was heated
2. 2
   温度to reflux for 24 h
3. 3
   浓缩concentrated under vacuum
4. 4
   其他The resulting mixture was absorbed onto silica
5. 5
   其他was purified by flash chromatography
6. 6
   洗涤eluted with 3:1 hexanes
7. 7
   其他The desired fractions were collected
8. 8
   浓缩concentrated under vacuum
9. 9
   其他to afford a solid which
10. 10
    其他was dried under high vacuum

实验过程

A solution of methyl 3,5-dibromo-4-methylbenzoate (5 g, 16.24 mmol) in carbon tetrachloride (50 mL) was treated with N-bromosuccinamide (3.6 g, 20.23 mmol) and 2,2′-azobisisobutyronitrile (0.56 g, 3.410 mmol). The reaction mixture was heated to reflux for 24 h. The reaction was cooled to room temperature and concentrated under vacuum. The resulting mixture was absorbed onto silica and was purified by flash chromatography using silica gel eluted with 3:1 hexanes: ethyl acetate. The desired fractions were collected and concentrated under vacuum to afford a solid which was dried under high vacuum to afford 3,5-dibromo-4-bromomethyl-benzoic acid methyl ester (57) (6.22 g, 99%) as a yellow solid; LRMS for C9H7Br3O2 (M+Na) m/z=407. MW=386.8669, Exact Mass=383.7996

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