Benzyl Bromide → 1-Bromo-4-phenylmethoxybenzene

HRID 2256031Notes

Reaction equation

HRID 2256031 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([OH:8])=[CH:4][CH:3]=1.C(=O)([O-])[O-].[K+].[K+].[CH2:15](Br)[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1>CN(C)C=O.O.CCCCCC>[CH2:15]([O:8][C:5]1[CH:6]=[CH:7][C:2]([Br:1])=[CH:3][CH:4]=1)[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1

Participants

7

Reactant 3

HCID 7498Benzyl BromideHCID 78084-BromophenolHCID 11430Potassium Carbonate

Product 1

HCID 1388351-Bromo-4-phenylmethoxybenzeneYield 88.9%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 8058HexaneSolvent

Procedure

A solution of 4-bromophenol (17.3 g) in dimethylformamide (200 mL) was treated with potassium carbonate (15.2 g) followed by benzyl bromide (17.1 g 11.9 mL). After stirring for 16 hours at ambient temperature, the reaction mixture was diluted with water and hexane. The aqueous layer was extracted with hexane:ether (5:1). The organic extracts were washed (water, 1N sodium hydroxide, brine), dried and evaporated to give the bromobenzene as a white solid (23.4 g); NMR (CDCl3): 5.03 (s, 2), 6.85 (dd, 2, J1 =5, J2 =2), 7.3-7.4 (m, 7); MS: m/z=263(M+1). This material was used in the next step without further purification.

Workup

  1. extractionThe aqueous layer was extracted with hexane:ether (5:1)
  2. washThe organic extracts were washed (water, 1N sodium hydroxide, brine)
  3. customdried
  4. customevaporated

Sources & evidence

ORD record
ord-c20aee0fbfc64aa5b135e236f59400f3
Source dataset
uspto-grants-1997_08
Patent number
US05654299

Reaction notes

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