Water → 1-(Benzyloxy)-2-bromobenzene

HRID 2256032Notes

Reaction equation

HRID 2256032 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.CCCCCC>[CH2:15]([O:8][C:3]1[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=1[Br:1])[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1

Participants

7

Reactant 4

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

Product 1

HCID 5618281-(Benzyloxy)-2-bromobenzeneYield 87.2%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8058HexaneSolvent

Procedure

A solution of 2-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 3 hours at the room temperature, the reaction mixture was diluted water and hexane. The aqueous layer was extracted with hexane; and the organic layers were washed (water, 1N sodium hydroxide, brine), dried and evaporated to give the product as a colorless oil (22.94 g). This material was fractionally distilled under reduced pressure to afford the bromobenzene (16.52 g); bp 110°-145° C. (1333 Pa); NMR (CDCl3): 5.17 (s, 2), 6.65 (d of t,1, J=8, J=1), 6.92-6.96 (d of d, 1, J=8, J=1), 7.19-7.26 (m, 1), 7.33-7.42 (m, 3), 7.46-7.50 (m, 2), 7.55 (d of d, 1, J=9, J=2). This material was used in the next step without further purification.

Workup

  1. extractionThe aqueous layer was extracted with hexane
  2. washand the organic layers were washed (water, 1N sodium hydroxide, brine)
  3. customdried
  4. customevaporated

Sources & evidence

ORD record
ord-475662ae38644b469f7758703bc5ad79
Source dataset
uspto-grants-1997_08
Patent number
US05654299

Reaction notes

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