反応 #2286319

反応方程式

methyl 3,5-dibromo-4-methylbenzoate

N-bromosuccinamide

2,2′-azobisisobutyronitrile

→

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

収率 99.0%

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

収率 99.0%

溶媒

carbon tetrachloride

反応条件

後処理

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

実験手順

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

出典