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

HRID 1748030Notes

Reaction equation

HRID 1748030 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-e465a99a4bda4edca134b5e90a6cf6cf
Source dataset
uspto-grants-2015_10
Patent number
US09150591B2

Reaction notes

Loading…