Sodium Iodide → 1-(Benzyloxy)-2-bromobenzene

HRID 260990Notes

Reaction equation

HRID 260990 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[OH:8].[CH2:9](Br)[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1.C(=O)([O-])[O-].[K+].[K+].[I-].[Na+]>C(#N)C>[CH2:9]([O:8][C:3]1[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=1[Br:1])[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1

Participants

6

Reactant 4

HCID 5238Sodium IodideHCID 72442-BromophenolHCID 7498Benzyl BromideHCID 11430Potassium Carbonate

Product 1

HCID 5618281-(Benzyloxy)-2-bromobenzeneYield 101.1%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A mixture of 2-bromophenol (1.50 g; 8.67 mmol), benzyl bromide (1.48 mg; 8.65 mmol). potassium carbonate (1.44 g; 10.41 mmol) and sodium iodide (catalytic amount) in 50 mL of acetonitrile was refluxed for 24 hours. After cooling, the solids were filtered off and the filtrate was concentrated. The crude residue was purified on a silica gel column (10% ethyl acetate hexane) to obtain 2.30 g (quantitative yield) of 2-benzyloxybromo- benzene, 1H NMR (CDCl3): δ 5.16 (s, 2H); 6.84 (t, 1H, J=7.6); 6.93 (d, 1H, J=8.3); 7.21-7.49(m, 6H); 7.56 (d, 1H, J=7.8).

Workup

  1. temperatureAfter cooling
  2. filtrationthe solids were filtered off
  3. concentrationthe filtrate was concentrated
  4. customThe crude residue was purified on a silica gel column (10% ethyl acetate hexane)

Sources & evidence

ORD record
ord-d1dc6145a76d45f58b0bd9831864ca28
Source dataset
uspto-grants-1996_06
Patent number
US05530157

Reaction notes

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