(4-Methoxyphenyl)(3-methylphenyl)methanone → (4-Hydroxyphenyl)(3-methylphenyl)methanone

HRID 1857201Notes

Reaction equation

HRID 1857201 reaction equation
[CH3:1][C:2]1[CH:3]=[C:4]([C:8]([C:10]2[CH:15]=[CH:14][C:13]([O:16]C)=[CH:12][CH:11]=2)=[O:9])[CH:5]=[CH:6][CH:7]=1.B(Br)(Br)Br.ClCCl>ClCCl>[CH3:1][C:2]1[CH:3]=[C:4]([C:8]([C:10]2[CH:11]=[CH:12][C:13]([OH:16])=[CH:14][CH:15]=2)=[O:9])[CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 12469466(4-Methoxyphenyl)(3-methylphenyl)methanoneHCID 22277759Boron tribromide dichloromethane

Product 1

HCID 22132621(4-Hydroxyphenyl)(3-methylphenyl)methanoneYield 56%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

4-Methoxyphenyl 3-methylphenyl ketone (603 mg) obtained in Example 131 was dissolved in dichloromethane (3 ml), a 1.0 M boron tribromide-dichloromethane solution (11 ml) was added while cooled in ice, and the admixture was stirred at room temperature for 22 hours, after which the reaction mixture was treated in the same manner as described in Example 121 to obtain 316 mg of the title compound (yield: 56%).

Workup

  1. temperaturewhile cooled in ice
  2. additionafter which the reaction mixture was treated in the same manner

Sources & evidence

ORD record
ord-4c29d032e89547b494d783a05917183c
Source dataset
uspto-grants-2000_11
Patent number
US06143764

Reaction notes

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