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

HRID 1622764Notes

Reaction equation

HRID 1622764 reaction equation
B(F)(F)F.CCOCC.[Br:10][C:11]1[CH:16]=[CH:15][C:14]([OH:17])=[CH:13][CH:12]=1.[CH:18]1[CH2:23][CH2:22][CH2:21][CH2:20][CH:19]=1>C1(C)C=CC=CC=1>[Br:10][C:11]1[CH:16]=[CH:15][C:14]([O:17][CH:18]2[CH2:23][CH2:22][CH2:21][CH2:20][CH2:19]2)=[CH:13][CH:12]=1

Participants

5

Reactant 3

HCID 78084-BromophenolHCID 8000Boron trifluoride etherateHCID 8079Cyclohexene

Product 1

HCID 111397141-Bromo-4-(cyclohexyloxy)benzene

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
40 °C

Procedure

Boron trifluoride etherate (5.83 mL) was added to a mixture of 4-bromophenol (39.8 g) and cyclohexene (187 mL) in toluene (160 mL) to form bright orange-red solution. The mixture was stirred at 40° C. under nitrogen for 5 hr. The mixture was quenched with 2N NaOH aq. (40 mL) and water at room temperature and extracted with EtOAc. The organic layer was separated, washed with water and brine, dried over anhydrous sodium sulfate and concentrated in vacuo. The residue was purified by column chromatography (silica gel, eluted with hexane) to give the title compound (46.3 g) as pale yellow oil.

Workup

  1. customto form bright orange-red solution
  2. customThe mixture was quenched with 2N NaOH aq. (40 mL) and water at room temperature
  3. extractionextracted with EtOAc
  4. customThe organic layer was separated
  5. washwashed with water and brine
  6. dry with materialdried over anhydrous sodium sulfate
  7. concentrationconcentrated in vacuo
  8. customThe residue was purified by column chromatography (silica gel, eluted with hexane)

Sources & evidence

ORD record
ord-24f9818a2d24481f96d1fc459bd165f8
Source dataset
uspto-grants-2014_07
Patent number
US08778934B2

Reaction notes

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