반응 #2286319

반응 방정식

methyl 3,5-dibromo-4-methylbenzoate

N-bromosuccinamide

2,2′-azobisisobutyronitrile

→

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

수율 99.0%

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

수율 99.0%

용매

carbon tetrachloride

반응 조건

후처리

1. 1
   온도The reaction mixture was heated
2. 2
   온도to reflux for 24 h
3. 3
   농축concentrated under vacuum
4. 4
   기타The resulting mixture was absorbed onto silica
5. 5
   기타was purified by flash chromatography
6. 6
   세척eluted with 3:1 hexanes
7. 7
   기타The desired fractions were collected
8. 8
   농축concentrated under vacuum
9. 9
   기타to afford a solid which
10. 10
    기타was dried under high vacuum

실험 절차

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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