Boron tribromide → (4-Bromophenyl)(4-hydroxyphenyl)methanone

HRID 1857237Notes

Reaction equation

HRID 1857237 reaction equation
COC1C=C2C(=CC=1OC)N=CC=C2[O:15][C:16]1[CH:21]=[CH:20][C:19]([C:22]([C:24]2[CH:29]=[CH:28][C:27](Cl)=[C:26](Cl)[CH:25]=2)=[O:23])=[CH:18][CH:17]=1.B(Br)(Br)[Br:33]>ClCCl>[Br:33][C:27]1[CH:28]=[CH:29][C:24]([C:22]([C:19]2[CH:20]=[CH:21][C:16]([OH:15])=[CH:17][CH:18]=2)=[O:23])=[CH:25][CH:26]=1

Participants

4

Reactant 2

HCID 25134Boron tribromideHCID 22132659HCID 22132659, compound

Product 1

HCID 4570728(4-Bromophenyl)(4-hydroxyphenyl)methanoneYield 85%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

4-Methoxyphenyl 4-bromophenyl ketone (1.65 g) obtained in Example 122 was dissolved in dichloromethane (20 ml), a solution of 1.0 M boron tribromide in dichloromethane (23 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 1.34 g of the title compound (yield: 85%).

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-19a56fa72b7b4e2c911f39924cf4b1ae
Source dataset
uspto-grants-2000_11
Patent number
US06143764

Reaction notes

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