4-Bromophenol → 1-Bromo-4-(cyclobutyloxy)benzene

HRID 922561Notes

Reaction equation

HRID 922561 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([OH:8])=[CH:4][CH:3]=1.[CH:9]1(Br)[CH2:12][CH2:11][CH2:10]1.C([O-])([O-])=O.[K+].[K+]>CN(C=O)C>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][CH:9]2[CH2:12][CH2:11][CH2:10]2)=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 78084-BromophenolHCID 11430Potassium CarbonateHCID 78110Bromocyclobutane

Product 1

HCID 679879981-Bromo-4-(cyclobutyloxy)benzene

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
120 °C

Procedure

The mixture of 2.50 g (14.5 mmol) of 4-bromophenol, 2.04 ml (21.7 mmol) of cyclobutyl bromide and 7.99 g (57.8 mmol) of K2CO3 in 25 ml DMF is stirred at 120° C. over night. The reaction mixture is extracted with water and EtOAc. The organic layer is dried, filtered and the solvent is removed in vacuo.

Workup

  1. extractionThe reaction mixture is extracted with water and EtOAc
  2. customThe organic layer is dried
  3. filtrationfiltered
  4. customthe solvent is removed in vacuo

Sources & evidence

ORD record
ord-b2861fa63ec54c5ea13073049c443bb2
Source dataset
uspto-grants-2016_03
Patent number
US09278954B2

Reaction notes

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