N-bromobutanimide → 1-Bromo-3-(bromomethyl)-2-methoxybenzene
Reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([CH3:8])[C:3]=1[O:9][CH3:10].C1C(=O)N([Br:18])C(=O)C1>C(Cl)(Cl)(Cl)Cl>[Br:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([CH2:8][Br:18])[C:3]=1[O:9][CH3:10]Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 80 °C
Procedure
1-Bromo-3-methyl-2-(methyloxy)benzene (30.3 g, 0.15 mol), NBS (28.2 g, 0.16 mol), and BPO (1.83 g, 7.55 mmol) were suspended in 300 mL of CCl4, and the mixture was heated to 80° C. over night. After cooling to room temperature, the solution was filtrated and the solid was washed with CCl4 (30 mL×2). The filtrate was washed with NaHSO3 (aq. 250 mL×2), Na2CO3 (aq. 100 mL×2), brine (100 mL) and dried over Na2SO4. After removing the solvent, 41.4 g of the crude product was obtained (yield: 97.9%).
Workup
- temperatureAfter cooling to room temperature
- filtrationthe solution was filtrated
- washthe solid was washed with CCl4 (30 mL×2)
- washThe filtrate was washed with NaHSO3 (aq. 250 mL×2), Na2CO3 (aq. 100 mL×2), brine (100 mL)
- dry with materialdried over Na2SO4
- customAfter removing the solvent
Sources & evidence
- ORD record
- ord-4acff6b538bc4895aa01859aa888bc0d
- Source dataset
- uspto-grants-2011_12
- Patent number
- US08071588B2
Reaction notes
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