O-Cresol → 4-[1-(4-Bromophenyl)-1-ethylpropyl]-2-methylphenol

HRID 547066Notes

Reaction equation

HRID 547066 reaction equation
[C:1]1([CH3:8])[C:6]([OH:7])=[CH:5][CH:4]=[CH:3][CH:2]=1.[Br:9][C:10]1[CH:15]=[CH:14][C:13]([C:16](O)([CH2:19][CH3:20])[CH2:17][CH3:18])=[CH:12][CH:11]=1>FC(F)(F)C(O)=O>[Br:9][C:10]1[CH:15]=[CH:14][C:13]([C:16]([C:3]2[CH:4]=[CH:5][C:6]([OH:7])=[C:1]([CH3:8])[CH:2]=2)([CH2:19][CH3:20])[CH2:17][CH3:18])=[CH:12][CH:11]=1

Participants

4

Reactant 2

HCID 335O-CresolHCID 57443521HCID 57443521, compound

Product 1

HCID 574435224-[1-(4-Bromophenyl)-1-ethylpropyl]-2-methylphenolYield 94.4%

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

o-Cresol (890 mg, 8.23 mmol) was added to a solution of 3-(4-bromo-phenyl)-pentan-3-ol (Example 143-(1); 2.0 g, 8.23 mmol) in trifluoroacetic acid (20 mL), and the mixture was stirred at room temperature for five hours. Then, the reaction mixture was concentrated under reduced pressure. The resulting residue was purified by silica gel chromatography (hexane:ethyl acetate=100:0 to 30:70) to give the target compound as a colorless oil (2.59 g, 94%).

Workup

  1. concentrationThen, the reaction mixture was concentrated under reduced pressure
  2. customThe resulting residue was purified by silica gel chromatography (hexane:ethyl acetate=100:0 to 30:70)

Sources & evidence

ORD record
ord-d5c79224be154965ac93dc701bf00a76
Source dataset
uspto-grants-2011_05
Patent number
US07935688B2

Reaction notes

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