تفاعل #2286319

معادلة التفاعل

methyl 3,5-dibromo-4-methylbenzoate

N-bromosuccinamide

2,2′-azobisisobutyronitrile

→

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

المردود 99.0%

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

المردود 99.0%

المذيبات

carbon tetrachloride

ظروف التفاعل

المعالجة

1. 1
   درجة الحرارةThe reaction mixture was heated
2. 2
   درجة الحرارةto reflux for 24 h
3. 3
   تركيزconcentrated under vacuum
4. 4
   أخرىThe resulting mixture was absorbed onto silica
5. 5
   أخرىwas purified by flash chromatography
6. 6
   غسيلeluted with 3:1 hexanes
7. 7
   أخرىThe desired fractions were collected
8. 8
   تركيزconcentrated under vacuum
9. 9
   أخرىto afford a solid which
10. 10
    أخرىwas dried under high vacuum

الإجراء التجريبي

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

المصدر