2-Bromophenol → 1-Bromo-2-(3-methylbutoxy)benzene

HRID 422053Notes

Reaction equation

HRID 422053 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[OH:8].Br[CH2:10][CH2:11][CH:12]([CH3:14])[CH3:13].C(=O)([O-])[O-].[K+].[K+]>C(#N)C>[Br:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[O:8][CH2:10][CH2:11][CH:12]([CH3:14])[CH3:13]

Participants

5

Reactant 3

HCID 72442-BromophenolHCID 78911-Bromo-3-methylbutaneHCID 11430Potassium Carbonate

Product 1

HCID 283695461-Bromo-2-(3-methylbutoxy)benzeneYield 93%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
80 °C

Procedure

A 500 mL of round-bottom flask was charged with 2-bromophenol (43 g, 0.25 mol), 1-bromo-3-methylbutane (41 mL, 0.325 mol), acetonitrile (200 mL) and potassium carbonate (52 g). The reaction mixture was heated to 80° C. with stirring overnight. The reaction was cooled and filtered, and washed with acetonitrile. The filtrate was concentrated in vacuo. Vacuum distillation of the residue yielded 1-bromo-2-(isopentyloxy)benzene (83-86° C., 56 g, 93% yield).

Workup

  1. temperatureThe reaction was cooled
  2. filtrationfiltered
  3. washwashed with acetonitrile
  4. concentrationThe filtrate was concentrated in vacuo
  5. distillationVacuum distillation of the residue

Sources & evidence

ORD record
ord-1bafd11df4aa43b08ce8aa61bc6cf586
Source dataset
uspto-grants-2012_01
Patent number
US08101625B2

Reaction notes

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