Benzyl Bromide → 4-Bromo-2-ethyl-6-methyl-1-benzyloxybenzene

HRID 599789Notes

Reaction equation

HRID 599789 reaction equation
[Br:1][C:2]1[CH:7]=[C:6]([CH3:8])[C:5]([OH:9])=[C:4]([CH2:10][CH3:11])[CH:3]=1.C([O-])([O-])=O.[K+].[K+].[CH2:18](Br)[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1>C(#N)C>[CH2:18]([O:9][C:5]1[C:6]([CH3:8])=[CH:7][C:2]([Br:1])=[CH:3][C:4]=1[CH2:10][CH3:11])[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1

Participants

5

Reactant 3

HCID 7498Benzyl BromideHCID 11430Potassium CarbonateHCID 220068384-Bromo-2-ethyl-6-methylphenol

Product 1

HCID 220068134-Bromo-2-ethyl-6-methyl-1-benzyloxybenzene

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A suspension of 39.8 g (185 mmol) 4-bromo-2-ethyl-6-methyl-phenol, 63.9 g (0.46 mmol) K2CO3 and 22.0 mL (185 mmol) benzyl bromide in 450 mL acetonitrile was refluxed for 3 h, cooled to RT and concentrated by evaporation i.vac. The residue was combined with EtOAc, the organic phase was washed with water and saturated NaCl solution, dried on Na2SO4 and concentrated by evaporation i.vac.

Workup

  1. temperaturewas refluxed for 3 h
  2. concentrationconcentrated by evaporation i.vac
  3. washthe organic phase was washed with water and saturated NaCl solution
  4. customdried on Na2SO4
  5. concentrationconcentrated by evaporation i.vac

Sources & evidence

ORD record
ord-385b5a6f544e4ec3beab58ee0b8fa295
Source dataset
uspto-grants-2011_03
Patent number
US07897603B2

Reaction notes

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