4-Bromophenol → 1-Bromo-4-[(prop-2-en-1-yl)oxy]benzene

HRID 744703Notes

Reaction equation

HRID 744703 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([OH:8])=[CH:4][CH:3]=1.[CH3:9][C:10](C)([O-])[CH3:11].[K+].C(Br)C=C>CS(C)=O.[Cl-].[Na+].O>[CH2:11]([O:8][C:5]1[CH:6]=[CH:7][C:2]([Br:1])=[CH:3][CH:4]=1)[CH:10]=[CH2:9]

Participants

6

Reactant 3

HCID 78084-BromophenolHCID 7841Allyl bromideHCID 23665647Potassium tert-butoxide

Product 1

HCID 2579441-Bromo-4-[(prop-2-en-1-yl)oxy]benzeneYield 79.3%

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 57417360Sodium chloride; waterSolvent

Procedure

To a solution of 4-bromophenol (43.25 g, 250 mmol) in DMSO (500 mls) was added potassium t-butoxide (32.26 g, 287.5 mmol) and the mixture was stirred for 20 mins. Allyl bromide (36.29 g, 300 mmol) was then added dropwise and the reaction was stirred for 1 hr. It was then diluted with brine (2 liters) and extracted with ethylacetate (3×2 liters) The organics were combined, dried with MgSO4 and concentrated. The crude residue was distilled (b.p.=157° C. at 30 mm Hg) to afford 42.25 g (79%) of 4-allyloxybromobenzene as a colorless oil.

Workup

  1. stirringthe reaction was stirred for 1 hr
  2. extractionextracted with ethylacetate (3×2 liters) The
  3. dry with materialdried with MgSO4
  4. concentrationconcentrated
  5. distillationThe crude residue was distilled (b.p.=157° C. at 30 mm Hg)

Sources & evidence

ORD record
ord-7e3ac261c1bd46cfae3ffbe72e7dd03d
Source dataset
uspto-grants-1996_09
Patent number
US05559144

Reaction notes

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