Water → Methyl 4-Bromo-3-(bromomethyl)benzoate
Reaction equation
[Br:1][C:2]1[CH:11]=[CH:10][C:5]([C:6]([O:8][CH3:9])=[O:7])=[CH:4][C:3]=1[CH3:12].C1C(=O)N([Br:20])C(=O)C1.O>C(Cl)(Cl)Cl>[Br:1][C:2]1[CH:11]=[CH:10][C:5]([C:6]([O:8][CH3:9])=[O:7])=[CH:4][C:3]=1[CH2:12][Br:20]Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 70 °C
Procedure
To a solution of methyl 4-bromo-3-methylbenzoate (50 g; 218 mmol) in CHCl3 (1 L) were added NBS (46.6 g; 262 mmol) in one portion and α,α′-azoisobutyronitrile (0.72 g; 4.37 mmol). The reaction mixture was stirred at 70° C. for 2 days. It was cooled down to RT and water was added. The organic layer was washed with aq. NaHCO3, then brine, dried over MgSO4 and concentrated in vacuo. The residue was washed with n-pentane to afford the title compound as a yellow solid. 1H NMR (DMSO-d6) δ 8.24 (d, J=1.9 Hz, 1H), 7.88-7.82 (m, 2H), 4.87 (s, 2H), 3.91 (s, 3H). HPLC (Method A): Rt 4.44 min (purity 97.9%).
Workup
- temperatureIt was cooled down to RT
- washThe organic layer was washed with aq. NaHCO3
- dry with materialbrine, dried over MgSO4
- concentrationconcentrated in vacuo
- washThe residue was washed with n-pentane
Sources & evidence
- ORD record
- ord-5b0b6aec87434f7abf524381b55548b7
- Source dataset
- uspto-grants-2014_06
- Patent number
- US08741923B2
Reaction notes
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