Phenol → 4-[1-(4-Bromo-3-methyl-phenyl)-1-ethyl-propyl]-phenol

HRID 546875Notes

Reaction equation

HRID 546875 reaction equation
[C:1]1([OH:7])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[Br:8][C:9]1[CH:14]=[CH:13][C:12]([C:15](O)([CH2:18][CH3:19])[CH2:16][CH3:17])=[CH:11][C:10]=1[CH3:21]>FC(F)(F)C(O)=O>[Br:8][C:9]1[CH:14]=[CH:13][C:12]([C:15]([C:4]2[CH:5]=[CH:6][C:1]([OH:7])=[CH:2][CH:3]=2)([CH2:18][CH3:19])[CH2:16][CH3:17])=[CH:11][C:10]=1[CH3:21]

Participants

4

Reactant 2

HCID 996PhenolHCID 574330783-(4-Bromo-3-methyl-phenyl)-pentan-3-ol

Product 1

HCID 574434914-[1-(4-Bromo-3-methyl-phenyl)-1-ethyl-propyl]-phenolYield 75.2%

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

Phenol (732 mg, 7.78 mmol) was added to a solution of 3-(4-bromo-3-methyl-phenyl)-pentan-3-ol (Example 38-(1); 2.0 g, 7.78 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, 40 minutes) to give the target compound as a colorless oil (1.95 g, 75%).

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, 40 minutes)

Sources & evidence

ORD record
ord-cd90f3db0fa54c9d86389ab93a295b3f
Source dataset
uspto-grants-2011_05
Patent number
US07935688B2

Reaction notes

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