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3-Phenoxytoluene → 1-Bromo-2-methyl-4-phenoxybenzene

HRID 51535
Notes
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Reaction equation

HRID 51535 reaction equation
[O:1]([C:8]1[CH:9]=[C:10]([CH3:14])[CH:11]=[CH:12][CH:13]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[Br:15]N1C(=O)CCC1=O>C(#N)C>[C:2]1([O:1][C:8]2[CH:13]=[CH:12][C:11]([Br:15])=[C:10]([CH3:14])[CH:9]=2)[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

4

Reactant 2

HCID 191653-PhenoxytolueneHCID 67184N-bromobutanimide

Product 1

HCID 128585521-Bromo-2-methyl-4-phenoxybenzeneYield 97.8%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A mixture of 3-phenoxytoluene (2.5 g, 0.0136 mol) and N-bromosuccinimide (2.54 g, 0.0142 mol) was stirred in acetonitrile (20 mL) for 2.5 hours under an atmosphere of nitrogen. The solvent was removed under reduced pressure. Carbon tetrachloride was added to the residue and the resulting solid was removed by filtration. The filtrate was concentrated to yield 4-bromo-3-methylphenyl phenyl ether as yellow oil (3.5 g, 0.0133 mol):

Workup

  1. customThe solvent was removed under reduced pressure
  2. additionCarbon tetrachloride was added to the residue
  3. customthe resulting solid was removed by filtration
  4. concentrationThe filtrate was concentrated

Sources & evidence

ORD record
ord-41372e57b62d4ee7b9f74314c3d1de09
Source dataset
uspto-grants-2004_03
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US06713474B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes