2-Bromophenol → 1-(Benzyloxy)-2-bromobenzene

HRID 2256054Notes

Reaction equation

HRID 2256054 reaction equation
C(=O)([O-])[O-].[K+].[K+].[Br:7][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=1[OH:14].[CH2:15](Br)[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1>CN(C)C=O.O>[Br:7][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=1[O:14][CH2:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1

Participants

6

Reactant 3

HCID 72442-BromophenolHCID 7498Benzyl BromideHCID 11430Potassium Carbonate

Product 1

HCID 5618281-(Benzyloxy)-2-bromobenzene

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

A suspension of potassium carbonate (15.2 g) in 200 mL of dimethylformamide containing 2-bromophenol (14.9 g) was treated with benzyl bromide (17.1 g). After stirring for 3 hours, the reaction mixture was diluted with water and extracted with hexane. The hexane layer was washed with water, 1N sodium hydroxide solution and brine, dried over sodium sulfate and evaporated to afford the crude product as an oil. This material was purified by fractional distillation under reduced pressure to afford the pure ether (16.52 g); bp 110°-145° C. (133 Pa); MS: 269; NMR: 5.2 (s, 2), 6.8-6.9 (d, t, J1 =7.5, J2 =1.3, 1), 6.9-7.0 (d,d, J1 =8, J2 =1.3, 1), 7.2-7.4 (m, 7), 7.5 (m, 2), 7.5-7.6 (d,d, J1 =8, J2 =1.6, 1).

Workup

  1. extractionextracted with hexane
  2. washThe hexane layer was washed with water, 1N sodium hydroxide solution and brine
  3. dry with materialdried over sodium sulfate
  4. customevaporated
  5. customto afford the crude product as an oil
  6. distillationThis material was purified by fractional distillation under reduced pressure
  7. customto afford the pure ether (16.52 g)

Sources & evidence

ORD record
ord-cd63d88c6a004c77985882249b0b1c37
Source dataset
uspto-grants-1997_08
Patent number
US05654299

Reaction notes

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