Water → 1-(Benzyloxy)-2-bromobenzene

HRID 1107301Notes

Reaction equation

HRID 1107301 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+].O>CN(C)C=O>[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 962WaterHCID 72442-BromophenolHCID 7498Benzyl BromideHCID 11430Potassium Carbonate

Product 1

HCID 5618281-(Benzyloxy)-2-bromobenzeneYield 19.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 2-bromophenol (10 g, 57.8 mmol), benzyl bromide (27.5 ml, 0.23 mol) and potassium carbonate (64 g, 0.462 mol) in N,N-dimethylformamide (70 ml) was stirred at room temperature for 72 hours. The suspension was poured into water (500 ml) and extracted with ethyl acetate (2×300 ml). The combined organic fractions were washed with water (300 ml), dried (Na2SO4) and the solvent was evaporated under reduced pressure. The residue was purified by flash column chromatography on silica gel, eluting with hexane/EtOAc (98:2) to give the title compound as a colourless oil (2.9 g). 1H NMR (250 MHz, CDCl3) δ 7.58-7.19 (8H, m), 6.95-6.81 (2H, m), and 5.16 (2H, m).

Workup

  1. extractionextracted with ethyl acetate (2×300 ml)
  2. washThe combined organic fractions were washed with water (300 ml)
  3. dry with materialdried (Na2SO4)
  4. customthe solvent was evaporated under reduced pressure
  5. customThe residue was purified by flash column chromatography on silica gel
  6. washeluting with hexane/EtOAc (98:2)

Sources & evidence

ORD record
ord-d3406ed4512742829284721972f472f9
Source dataset
uspto-grants-2000_05
Patent number
US06060469

Reaction notes

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