N-bromobutanimide → Methyl 2-(bromomethyl)-5-ethoxybenzoate
Reaction equation
[CH2:1]([O:3][C:4]1[CH:5]=[CH:6][C:7]([CH3:14])=[C:8]([CH:13]=1)[C:9]([O:11][CH3:12])=[O:10])[CH3:2].C1C(=O)N([Br:22])C(=O)C1>C(Cl)(Cl)(Cl)Cl.C(Cl)Cl.[Cl-].[Na+].O>[Br:22][CH2:14][C:7]1[CH:6]=[CH:5][C:4]([O:3][CH2:1][CH3:2])=[CH:13][C:8]=1[C:9]([O:11][CH3:12])=[O:10]Participants
6
Conditions
- Temperature
- 80 °C
Procedure
To a solution of methyl 5-ethoxy-2-methylbenzoate (134b, 0.700 g, 3.61 mmol) in CCl4 (12 mL) was added BPO (18.0 mg, 0.0720 mmol) and NBS (0.706 g, 3.97 mmol) at room temperature. The resulting mixture was heated at 80° C. for 12 hours under N2 atmosphere. The mixture was diluted with CH2Cl2 (10 mL) and brine (3 mL). The organic layer was separated and washed with NaHCO3 (2 N, 10 mL), H2O (5 mL) and brine (5 mL), dried over Na2SO4 and concentrated under vacuum. The residue was purified by column chromatography (petroleum ether/EtOAc=5:1) to give methyl 2-(bromomethyl)-5-ethoxybenzoate (134c, 0.85 g, 86%) as yellow liquid.
Workup
- customThe organic layer was separated
- washwashed with NaHCO3 (2 N, 10 mL), H2O (5 mL) and brine (5 mL)
- dry with materialdried over Na2SO4
- concentrationconcentrated under vacuum
- customThe residue was purified by column chromatography (petroleum ether/EtOAc=5:1)
Sources & evidence
- ORD record
- ord-9039af9cf5a4456791bd97a9e6725b39
- Source dataset
- uspto-grants-2015_05
- Patent number
- US09040515B2
Reaction notes
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