Water → 1-(Benzyloxy)-2-bromobenzene

HRID 1420833Notes

Reaction equation

HRID 1420833 reaction equation
[CH2:1](Br)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[Br:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=1[OH:16].C(=O)([O-])[O-].[K+].[K+].O>CN(C=O)C>[CH2:1]([O:16][C:11]1[CH:12]=[CH:13][CH:14]=[CH:15][C:10]=1[Br:9])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 962WaterHCID 72442-BromophenolHCID 7498Benzyl BromideHCID 11430Potassium Carbonate

Product 1

HCID 5618281-(Benzyloxy)-2-bromobenzene

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Benzyl bromide (27.5 ml) was added to a mixture of 2-bromophenol (10 g, 58 mmol) and potassium carbonate (64 g) in DMF (70 ml) and the mixture was stirred at room temperature for 72 h. The mixture was poured into water and extracted with ethyl acetate (2×). The combined organic fractions were washed with water, 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 (2.9 g). 1H NMR (250 MHz, CDCl3) δ7.58-7.20 (7 H, m), 6.94 (1 H, d 7.9 Hz), 6.84 (1 H, t, J 7.9 Hz), and 5.16 (2 H, s).

Workup

  1. extractionextracted with ethyl acetate (2×)
  2. washThe combined organic fractions were washed with water
  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-d6c08dec671c4274a03a161abb3a1ed7
Source dataset
uspto-grants-2000_06
Patent number
US06071927

Reaction notes

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