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

HRID 1936336Notes

Reaction equation

HRID 1936336 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+].C(C(C)=O)C>O1CCCC1>[CH2:1]([O:22][C:19]1[CH:18]=[CH:17][C:16]([C:13]2[CH:14]=[CH:15][C:10]([Br:9])=[CH:11][CH:12]=2)=[CH:21][CH:20]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=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 8028TetrahydrofuranSolvent

Procedure

First, 25.0 g of benzyl bromide, 36.42 g of 4′-bromo-4-hydroxybiphenyl, 36.4 g of potassium carbonate, and 300 ml of methyl ethyl ketone were put in a1 flask, and stirred under reflux for six hours. After the reaction, 300 ml of tetrahydrofuran was added to the reaction solution, and a mixture was cooled to ambient temperature. Insoluble material was filtered off, and toluene was added to the filtrate to separate an organic layer. The organic layer was washed with a saturated brine and dried with sodium sulfate. The solvent was then distilled off. The residue was recrystallized from acetone, to obtain 42.56 g (Y: 85.8%) of 4-benzyloxy-4′-bromobiphenyl. The purity of the resultant compound was 99.0% as measured by GC.

Workup

  1. temperatureunder reflux for six hours
  2. additionwas added to the reaction solution
  3. filtrationInsoluble material was filtered off
  4. additiontoluene was added to the filtrate
  5. customto separate an organic layer
  6. washThe organic layer was washed with a saturated brine
  7. dry with materialdried with sodium sulfate
  8. distillationThe solvent was then distilled off
  9. customThe residue was recrystallized from acetone

Sources & evidence

ORD record
ord-ca6103f2dd4f45f2894ab0de8930d9e6
Source dataset
uspto-grants-2002_05
Patent number
US06388146B1

Reaction notes

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