Hydrogen Bromide → 4-Bromo-2-cyclohexyl-phenol

HRID 2404877

Reaction equation

HRID 2404877 reaction equation
[CH:1]1([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=2[OH:13])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[BrH:14].CS(C)=O>C(O)(=O)C.O>[Br:14][C:11]1[CH:10]=[CH:9][C:8]([OH:13])=[C:7]([CH:1]2[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6]2)[CH:12]=1

Participants

6

Reactant 3

HCID 260Hydrogen BromideHCID 679Dimethyl SulfoxideHCID 8396o-Cyclohexylphenol

Product 1

HCID 221345164-Bromo-2-cyclohexyl-phenolYield 93%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolvent2×HCID 962WaterSolvent

Procedure

To a stirring solution of 2-cyclohexylphenol (26.0 g, 146.8 mmol) in glacial acetic acid (100 mL) was added HBr in acetic acid (150 mL of 33% w/w,) and H2O (52 mL), followed by the dropwise addition of DMSO (100 mL) over 10 min. The reaction was then carefully quenched with saturated NaHCO3 and concentrated in vacuo. The residue was brought up in ether (400 mL), washed with water (2×100 mL) and brine (1×100 mL), and dried over anhydrous Na2SO4, filtered and concentration to yield a crude oil that was purified by silica gel column chromatography, using 15-30% EtOAc/hexane gradient to yield 4-bromo-2-cyclohexyl-phenol (35.0 g, 93%)

Workup

  1. customThe reaction was then carefully quenched with saturated NaHCO3
  2. concentrationconcentrated in vacuo
  3. washwashed with water (2×100 mL) and brine (1×100 mL)
  4. dry with materialdried over anhydrous Na2SO4
  5. filtrationfiltered
  6. concentrationconcentration
  7. customto yield a crude oil that
  8. customwas purified by silica gel column chromatography

Sources & evidence

ORD record
ord-9a5ac49ca563407fbf7fa9ac68ba84e4
Source dataset
uspto-grants-2014_08
Patent number
US08802700B2

Linked notes

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