Water → 1-(Benzyloxy)-2-bromobenzene

HRID 1639277Notes

Reaction equation

HRID 1639277 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[OH:8].C(=O)([O-])[O-].[K+].[K+].[CH2:15](Br)[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1.O>CN(C)C=O>[Br:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[O:8][CH2:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1

Participants

6

Reactant 4

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

Product 1

HCID 5618281-(Benzyloxy)-2-bromobenzeneYield 94%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a mixture of 7.45 g (43.1 mmol, Aldrich) of 2-bromophenol, and 6.9 g (50 mmol) of anhydrous potassium carbonate in 25 mL dimethylformamide (DMF) (Burdick and Jackson) heated to 80° was added dropwise 7.37 g (43.1 mmol, Aldrich) of benzyl bromide over 10 minutes. The reaction mixture was stirred at 80° for 1 hour then cooled to room temperature, added to 100 mL of water and extracted with two 50 mL portions of 1:5 ethyl ether/hexane. The organic extracts were combined, washed with 50 mL of 1M aqueous NaOH solution, 50 mL of water, dried (magnesium sulfate) and concentrated in vacuo to afford 10.6 g (40.3 mmol, 94%) of title compound as a colorless liquid.

Workup

  1. temperatureheated to 80°
  2. extractionextracted with two 50 mL portions of 1:5 ethyl ether/hexane
  3. washwashed with 50 mL of 1M aqueous NaOH solution, 50 mL of water
  4. dry with materialdried (magnesium sulfate)
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-1d74855810c04ed8805da9ed606901c3
Source dataset
uspto-grants-1989_11
Patent number
US04883809

Reaction notes

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