Water → Methyl 4-Bromo-3-(bromomethyl)benzoate
Reaction equation
C1C(=O)N([Br:8])C(=O)C1.CC(N=NC(C#N)(C)C)(C#N)C.[Br:21][C:22]1[CH:31]=[CH:30][C:25]([C:26]([O:28][CH3:29])=[O:27])=[CH:24][C:23]=1[CH3:32].O>C(Cl)(Cl)Cl>[Br:21][C:22]1[CH:31]=[CH:30][C:25]([C:26]([O:28][CH3:29])=[O:27])=[CH:24][C:23]=1[CH2:32][Br:8]Participants
6
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 70 °C
Procedure
NBS (46.6 g, 262 mmol) and AIBN (0.72 g, 4.4 mmol) were added in one portion into a solution of methyl 4-bromo-3-methylbenzoate (50.0 g, 218 mmol) in CHCl3 (1 L) under N2. 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 solution of NaHCO3 (50 mL), water (350 mL) and brine (500 mL). The organic layer was dried (MgSO4) and concentrated under reduced pressure. The residue was washed with pentane (2×500 mL) affording the title compound as a yellow solid. HPLC (Method A), Rt 4.9 min (Purity: 98.2%). 1H NMR (DMSO-d6, 300 MHz) δ 8.24 (d, J=1.9 Hz, 1H), 7.85 (m, 2H), 4.87 (s, 2H), 3.91 (s, 3H).
Workup
- temperatureThe reaction mixture was cooled to RT
- washThe organic layer was washed with a saturated solution of NaHCO3 (50 mL), water (350 mL) and brine (500 mL)
- dry with materialThe organic layer was dried (MgSO4)
- concentrationconcentrated under reduced pressure
- washThe residue was washed with pentane (2×500 mL)
Sources & evidence
- ORD record
- ord-56b7e8e180c34f548706a68478035128
- Source dataset
- uspto-grants-2014_07
- Patent number
- US08791142B2
Reaction notes
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