Boron tribromide → (4-Hydroxyphenyl)(2-methylphenyl)methanone

HRID 1857196Notes

Reaction equation

HRID 1857196 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]([C:10]1[CH:15]=[CH:14][C:13]([O:16]C)=[CH:12][CH:11]=1)=[O:9].B(Br)(Br)Br>C(Cl)(Cl)Cl.ClCCl>[CH3:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]([C:10]1[CH:11]=[CH:12][C:13]([OH:16])=[CH:14][CH:15]=1)=[O:9]

Participants

5

Reactant 2

HCID 25134Boron tribromide2×HCID 6145214-METHOXY-2'-METHYLBENZOPHENONE

Product 1

HCID 22132708(4-Hydroxyphenyl)(2-methylphenyl)methanoneYield 96.4%

Reagents, catalysts & solvents 2

HCID 6212ChloroformSolventHCID 6344DichloromethaneSolvent2×

Procedure

4-Methoxyphenyl 2-methylphenyl ketone (1.660 g) obtained in Example 125 was dissolved in chloroform (10 ml), a solution of 1.0 M boron tribromide in dichloromethane (29 ml) was added while cooled in ice, and the admixture was stirred at room temperature overnight. A solution of 1.0 M boron tribromide in dichloromethane (15 ml) was further added, and the admixture was stirred at room temperature for 2 days. The reaction mixture was then treated in the same manner as described in Example 121 to obtain 1.501 g of the title compound (yield: 96%).

Workup

  1. temperaturewhile cooled in ice
  2. stirringthe admixture was stirred at room temperature for 2 days
  3. additionThe reaction mixture was then treated in the same manner

Sources & evidence

ORD record
ord-23f6b699dc1a4c788bf8013cd8c9e339
Source dataset
uspto-grants-2000_11
Patent number
US06143764

Reaction notes

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