N-bromobutanimide → 1,6-Dibromo-2-methoxy-naphthalene
Reaction equation
[Br:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[CH:8]=[C:7]([O:12][CH3:13])[CH:6]=[CH:5]2.C1C(=O)N([Br:21])C(=O)C1>C1COCC1>[Br:21][C:8]1[C:9]2[C:4](=[CH:3][C:2]([Br:1])=[CH:11][CH:10]=2)[CH:5]=[CH:6][C:7]=1[O:12][CH3:13]Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
6-Bromo-2-methoxynaphthalene (5.9 g, 24.81 mmol, 1 eq) and NBS (4.41, 24.81 mmol, 1 eq) are boiled in 50 ml of THF under reflux for 2 h. After washing with 1 N HCl, the organic phase is dried over magnesium sulfate, filtered and concentrated in vacuum on a rotary evaporator. The compound is obtained in quantitative yield (7.8 g).
Workup
- temperatureunder reflux for 2 h
- washAfter washing with 1 N HCl
- dry with materialthe organic phase is dried over magnesium sulfate
- filtrationfiltered
- concentrationconcentrated in vacuum on a rotary evaporator
- customThe compound is obtained in quantitative yield (7.8 g)
Sources & evidence
- ORD record
- ord-7529570b0a404868bf016225143e0a81
- Source dataset
- uspto-grants-2013_10
- Patent number
- US08546392B2
Reaction notes
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