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

HRID 409714Notes

Reaction equation

HRID 409714 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.O>[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

6

Reactant 3

HCID 78084-BromophenolHCID 11430Potassium CarbonateHCID 78110Bromocyclobutane

Product 1

HCID 679879981-Bromo-4-(cyclobutyloxy)benzene

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
120 °C

Procedure

2.50 g (14.5 mmol) 4-bromophenol, 2.05 mL (21.7 mmol) cyclobutylbromide and 7.99 g (57.8 mmol) K2CO3 are dissolved in 25 mL DMF and stirred at 120° C. for 12 h. Afterwards the reaction mixture is diluted with water and extracted with EtOAc. The organic layer is dried over MgSO4 and the solvent is removed in vacuo. The crude product is used without further purification.

Workup

  1. extractionextracted with EtOAc
  2. dry with materialThe organic layer is dried over MgSO4
  3. customthe solvent is removed in vacuo
  4. customThe crude product is used without further purification

Sources & evidence

ORD record
ord-86f47b0fec1549db966c451350fe63cd
Source dataset
uspto-grants-2014_06
Patent number
US08759528B2

Reaction notes

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