Benzyl Bromide → 1-Bromo-4-phenylmethoxybenzene

HRID 892855Notes

Reaction equation

HRID 892855 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([OH:8])=[CH:4][CH:3]=1.CC(C)([O-])C.[K+].[CH2:15](Br)[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1>CS(C)=O.[Cl-].[Na+].O>[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

6

Reactant 3

HCID 7498Benzyl BromideHCID 78084-BromophenolHCID 23665647Potassium tert-butoxide

Product 1

HCID 1388351-Bromo-4-phenylmethoxybenzeneYield 100.1%

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 57417360Sodium chloride; waterSolvent

Procedure

To a solution of 4-bromophenol (8.65 g, 50 mmol) in dimethylsulfoxide (100 mL) was added potassium t-butoxide (6.45 g, 57.5 mmol) and the mixture was stirred for 20 mins. Benzyl bromide (10.26 g, 60 mmol) was then added and the reaction was stirred for 1 hr. It was then diluted with brine (150 mL) and extracted with ethylacetate (3×200 mL). The organics were combined, dried with MgSO4 and concentrated. The resulting residue was distilled under vacuum (0.8 mm Hg) to afford 13.17 g of 4-benzyloxybromobenzene as a white solid (b.p. 150-155∞C).

Workup

  1. stirringthe reaction was stirred for 1 hr
  2. extractionextracted with ethylacetate (3×200 mL)
  3. dry with materialdried with MgSO4
  4. concentrationconcentrated
  5. distillationThe resulting residue was distilled under vacuum (0.8 mm Hg)

Sources & evidence

ORD record
ord-0531d8b49fa14a2f969aaab4d6a2e5ff
Source dataset
uspto-grants-1992_06
Patent number
US05120752

Reaction notes

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