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

HRID 491129Notes

Reaction equation

HRID 491129 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) benzylbromide in 450 mL acetonitrile was refluxed for 3 h, cooled to RT and evaporated down i.vac. The residue was combined with EtOAc, the organic phase was washed with water and saturated NaCl solution, dried over Na2SO4 and evaporated down i.vac.

Workup

  1. temperaturewas refluxed for 3 h
  2. customevaporated down i.vac
  3. washthe organic phase was washed with water and saturated NaCl solution
  4. dry with materialdried over Na2SO4
  5. customevaporated down i.vac

Sources & evidence

ORD record
ord-05011c4900ba42a5af190531dcb0f20b
Source dataset
uspto-grants-2009_05
Patent number
US07528129B2

Reaction notes

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