N-bromobutanimide → Methyl 2-(bromomethyl)-5-methoxybenzoate
Reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]([CH3:13])=[C:7]([CH:12]=1)[C:8]([O:10][CH3:11])=[O:9].[Br:14]N1C(=O)CCC1=O>ClC(Cl)(Cl)Cl.C(Cl)Cl.C(OOC(=O)C1C=CC=CC=1)(=O)C1C=CC=CC=1>[Br:14][CH2:13][C:6]1[CH:5]=[CH:4][C:3]([O:2][CH3:1])=[CH:12][C:7]=1[C:8]([O:10][CH3:11])=[O:9]Participants
6
Conditions
- Temperature
- 77 °C
Procedure
Step 1 A suspension of methyl 5-methoxy-2-methylbenzoate (1.00 g, 5.55 mmol), N-bromosuccinimide (1.037 g, 5.83 mmol) and benzoyl peroxide (81 mg, 0.333 mmol) in tetrachloromethane (10 mL) was heated at 77° C. for 3 h. The mixture was diluted with DCM, washed with NaHCO3 (aq), dried and concentrated to provide crude methyl 2-(bromomethyl)-5-methoxybenzoate as a light yellow solid (1.435 g), used without further purification. 1H NMR (400 MHz, chloroform-d) δ 7.48 (1 H, d, J=2.64 Hz), 7.37 (1 H, d, J=8.36 Hz), 7.02 (1 H, dd, J=8.58, 2.86 Hz), 4.93 (2 H, s), 3.95 (3 H, s), 3.85 (3 H, s).
Workup
- washwashed with NaHCO3 (aq)
- customdried
- concentrationconcentrated
Sources & evidence
- ORD record
- ord-70a4c3f303034717be2dd17bcb71878a
- Source dataset
- uspto-grants-2013_01
- Patent number
- US08362065B2
Reaction notes
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