N-bromobutanimide → 1,6-Dibromo-2-methoxynaphthalene

HRID 1035591Notes

Reaction equation

HRID 1035591 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

HCID 67184N-bromobutanimideHCID 787862-Bromo-6-methoxynaphthalene

Product 1

HCID 35030571,6-Dibromo-2-methoxynaphthalene

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

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

  1. temperatureunder reflux for 2 h
  2. washAfter washing with 1 N HCl
  3. dry with materialthe organic phase is dried over magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated in vacuum on a rotary evaporator
  6. 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

Loading…