Boron tribromide → HCID 22111472, compound

HRID 249278Notes

Reaction equation

HRID 249278 reaction equation
[F:1][C:2]1[C:17]([F:18])=[C:16]([F:19])[C:15]([F:20])=[C:14]([F:21])[C:3]=1[C:4]([C:6]1[CH:11]=[CH:10][C:9]([O:12]C)=[CH:8][CH:7]=1)=[O:5].B(Br)(Br)Br>C(Cl)CCl>[F:1][C:2]1[C:17]([F:18])=[C:16]([F:19])[C:15]([F:20])=[C:14]([F:21])[C:3]=1[C:4]([C:6]1[CH:11]=[CH:10][C:9]([OH:12])=[CH:8][CH:7]=1)=[O:5]

Participants

4

Reactant 2

HCID 25134Boron tribromideHCID 11044839HCID 11044839, compound

Product 1

HCID 22111472HCID 22111472, compoundYield 72.5%

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent2×

Procedure

A solution of 5.6 g of 2,3,4,5,6-pentafluoro-4'-methoxy-benzophenone in 100 ml of ethylene chloride was added dropwise at -7° under argon to a solution of 23.23 g of boron tribromide in 100 ml of ethylene chloride. The reaction mixture was warmed to room temperature and stirred at this temperature for 5 hours. The reaction mixture was poured into 200 ml of ice-cold water and extracted three times with 150 ml of methylene chloride each time. The combined extracts were washed with 200 ml of water and dried over magnesium sulphate. After evaporation of the solvent the residue was chromatographed on 900 g of silica gel with methylene chloride. There were obtained 3.87 g (72%) of 2,3,4,5,6-pentafluoro-4'-hydroxybenzophenone: m.p. 138°-140°.

Workup

  1. extractionextracted three times with 150 ml of methylene chloride each time
  2. washThe combined extracts were washed with 200 ml of water
  3. dry with materialdried over magnesium sulphate
  4. customAfter evaporation of the solvent the residue
  5. customwas chromatographed on 900 g of silica gel with methylene chloride

Sources & evidence

ORD record
ord-c9746cf5fff649b39abc4d3280e9412c
Source dataset
uspto-grants-1993_05
Patent number
US05214046

Reaction notes

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