Benzyl Bromide → 2-(Benzyloxy)-6-bromonaphthalene

HRID 48098

Reaction equation

HRID 48098 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[CH:8]=[C:7]([OH:12])[CH:6]=[CH:5]2.[CH2:13](Br)[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1>CN(C=O)C.C(=O)([O-])[O-].[Cs+].[Cs+]>[CH2:13]([O:12][C:7]1[CH:6]=[CH:5][C:4]2[C:9](=[CH:10][CH:11]=[C:2]([Br:1])[CH:3]=2)[CH:8]=1)[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1

Participants

5

Reactant 2

HCID 7498Benzyl BromideHCID 271446-Bromo-2-naphthalenol

Product 1

HCID 6405952-(Benzyloxy)-6-bromonaphthalene

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 10796Cesium carbonateSolvent

Procedure

To the commercially available 6-bromo-naphthalene-2-ol (1) (1 equi.) and benzyl bromide (2) (1 equi.) in DMF (3mL/mmole), cesium carbonate (1.25 equi.) was added at room temperature. The reaction mixture was stirred at that temperature for 24 h, quenched with water, extracted with ethyl acetate:hexane (1:1), washed with brine, over MgSO4, and concentrated in vacuo.

Workup

  1. customquenched with water
  2. extractionextracted with ethyl acetate:hexane (1:1)
  3. washwashed with brine, over MgSO4
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-2d89c4a6c19742cea11d66a9ead29487
Source dataset
uspto-grants-2004_03
Patent number
US06703082B1

Linked notes

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