Boron tribromide → (4-Hydroxyphenyl)(4-iodophenyl)methanone

HRID 1857234Notes

Reaction equation

HRID 1857234 reaction equation
[I:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([C:10]2[CH:15]=[CH:14][C:13]([O:16]C)=[CH:12][CH:11]=2)=[O:9])=[CH:4][CH:3]=1.B(Br)(Br)Br>ClCCl>[I:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([C:10]2[CH:15]=[CH:14][C:13]([OH:16])=[CH:12][CH:11]=2)=[O:9])=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 25134Boron tribromideHCID 22132674(4-Iodophenyl)(4-methoxyphenyl)methanone

Product 1

HCID 13453359(4-Hydroxyphenyl)(4-iodophenyl)methanoneYield 55%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

4-Methoxyphenyl 4-iodophenyl ketone (722 mg) obtained in Example 176 was dissolved in dichloromethane (20 ml), a solution of 1.0 M boron tribromide in dichloromethane (9 ml) was added while cooled in ice, and the admixture was stirred at room temperature overnight. The reaction mixture was then poured into ice water and partitioned between water and chloroform. The chloroform layer was dried with anhydrous magnesium sulfate and the solvent was removed by reduced-pressure distillation. The resulting residue was purified by column chromatography on silica gel eluting with hexane/ethyl acetate to obtain 380 mg of the title compound (yield: 55%).

Workup

  1. temperaturewhile cooled in ice
  2. custompartitioned between water and chloroform
  3. dry with materialThe chloroform layer was dried with anhydrous magnesium sulfate
  4. customthe solvent was removed by reduced-pressure distillation
  5. customThe resulting residue was purified by column chromatography on silica gel eluting with hexane/ethyl acetate

Sources & evidence

ORD record
ord-0b2926c948b84e1c80a9e346af6875ab
Source dataset
uspto-grants-2000_11
Patent number
US06143764

Reaction notes

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