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, to a solution of methyl 4-bromo-3-methylbenzoate (Aldrich 532878, 50.0 g, 218.3 mmol) in CHCl3 (1 L) were added NBS (46.6 g, 261.9 mmol) in one portion and α,α′-azoisobutyronitrile (0.72 g, 4.37 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 a saturated aqueous solution of NaHCO3 (500 mL), 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=1.91 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 a saturated aqueous solution of NaHCO3 (500 mL), water (340 mL)
- dry with materialbrine (500 mL), dried over MgSO4
- concentrationconcentrated
Sources & evidence
- ORD record
- ord-4a8aea6077e84a3ebb3a1b07f734e692
- Source dataset
- uspto-grants-2014_08
- Patent number
- US08815919B2
Reaction notes
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