Reaction #2286319

Reaction equation

methyl 3,5-dibromo-4-methylbenzoate

N-bromosuccinamide

2,2′-azobisisobutyronitrile

→

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

Yield 99.0%

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

Yield 99.0%

Solvents

carbon tetrachloride

Conditions

Workup

1. 1
   TemperatureThe reaction mixture was heated
2. 2
   Temperatureto reflux for 24 h
3. 3
   Concentrationconcentrated under vacuum
4. 4
   OtherThe resulting mixture was absorbed onto silica
5. 5
   Otherwas purified by flash chromatography
6. 6
   Washeluted with 3:1 hexanes
7. 7
   OtherThe desired fractions were collected
8. 8
   Concentrationconcentrated under vacuum
9. 9
   Otherto afford a solid which
10. 10
    Otherwas dried under high vacuum

Procedure

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

Source