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
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 70 °C
Procedure
Under N2 atmosphere, to a solution of methyl 4-bromo-3-methylbenzoate (Aldrich 532878, 50 g; 218 mmol) in CHCl3 (1 L) were added NBS (47 g; 262 mmol) in one portion and α,α′-azoisobutyronitrile (720 mg; 4.4 mmol). The mixture was stirred at 70° C. for 2 days. The reaction mixture was cooled to RT and water (500 mL) was added. The organic layer was washed with 50 mL NaHCO3 saturated solution, water (340 mL), then brine (500 mL), dried over MgSO4 and concentrated affording the title compound as a yellow solid. It was washed with pentane (2×500 mL) affording the title compound as a yellow solid. 1H NMR (DMSO-d6, 300 MHz) 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
- temperatureThe reaction mixture was cooled to RT
- washThe organic layer was washed with 50 mL NaHCO3 saturated solution, water (340 mL)
- dry with materialbrine (500 mL), dried over MgSO4
- concentrationconcentrated
Sources & evidence
- ORD record
- ord-8f760409e6e544f79d6ec0f5c8afd849
- Source dataset
- uspto-grants-2015_05
- Patent number
- US09029405B2
Reaction notes
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