Reacción #2286319

Ecuación de reacción

methyl 3,5-dibromo-4-methylbenzoate

N-bromosuccinamide

2,2′-azobisisobutyronitrile

→

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

Rendimiento 99.0%

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

Rendimiento 99.0%

Disolventes

carbon tetrachloride

Condiciones de reacción

Tratamiento posterior

1. 1
   TemperaturaThe reaction mixture was heated
2. 2
   Temperaturato reflux for 24 h
3. 3
   Concentraciónconcentrated under vacuum
4. 4
   OtroThe resulting mixture was absorbed onto silica
5. 5
   Otrowas purified by flash chromatography
6. 6
   Lavadoeluted with 3:1 hexanes
7. 7
   OtroThe desired fractions were collected
8. 8
   Concentraciónconcentrated under vacuum
9. 9
   Otroto afford a solid which
10. 10
    Otrowas dried under high vacuum

Procedimiento

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

Fuente