Methyl Ethyl Ketone → 4-(Benzyloxy)-4'-bromo-1,1'-biphenyl

HRID 2395203Notes

Reaction equation

HRID 2395203 reaction equation
[CH2:1](Br)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[Br:9][C:10]1[CH:15]=[CH:14][C:13]([C:16]2[CH:21]=[CH:20][C:19]([OH:22])=[CH:18][CH:17]=2)=[CH:12][CH:11]=1.C(=O)([O-])[O-].[K+].[K+].CC(=O)CC>O>[Br:9][C:10]1[CH:11]=[CH:12][C:13]([C:16]2[CH:21]=[CH:20][C:19]([O:22][CH2:1][C:2]3[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=3)=[CH:18][CH:17]=2)=[CH:14][CH:15]=1

Participants

6

Reactant 4

HCID 6569Methyl Ethyl KetoneHCID 7498Benzyl BromideHCID 11430Potassium CarbonateHCID 950934-Bromo-4'-hydroxybiphenyl

Product 1

HCID 224657734-(Benzyloxy)-4'-bromo-1,1'-biphenylYield 85.8%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

In a flask, 25 g of benzyl bromide, 36.4 g of 4-bromo-4'-hydroxybiphenyl, 40.4 g of potassium carbonate, and 300 ml of 2-butanone were placed, and stirred under reflux for 6 hours. The reaction solution was poured into water, and an organic layer was extracted with toluene. After the toluene layer was washed with water and dried over sodium sulfate anhydrous, the solvent was distilled away. The residue was recrystallized from acetone to give 42.5 g of 4-bromo-4'-benzyloxybiphenyl (Y: 85.8%). The purity of the compound thus obtained was 99.0% by GC.

Workup

  1. temperatureunder reflux for 6 hours
  2. extractionan organic layer was extracted with toluene
  3. washAfter the toluene layer was washed with water
  4. dry with materialdried over sodium sulfate anhydrous
  5. distillationthe solvent was distilled away
  6. customThe residue was recrystallized from acetone

Sources & evidence

ORD record
ord-4e6fdf25f52e4d74b6b00395ecf8c6f2
Source dataset
uspto-grants-1998_09
Patent number
US05814378

Reaction notes

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