Bromine → 1-(5-Bromo-2,4-dihydroxy-3-propylphenyl)ethan-1-one

HRID 2231462Notes

Reaction equation

HRID 2231462 reaction equation
[OH:1][C:2]1[C:7]([CH2:8][CH2:9][CH3:10])=[C:6]([OH:11])[CH:5]=[CH:4][C:3]=1[C:12](=[O:14])[CH3:13].[Br:15]Br>C(Cl)(Cl)Cl>[Br:15][C:5]1[C:6]([OH:11])=[C:7]([CH2:8][CH2:9][CH3:10])[C:2]([OH:1])=[C:3]([C:12](=[O:14])[CH3:13])[CH:4]=1

Participants

4

Reactant 2

HCID 24408BromineHCID 27751982',4'-Dihydroxy-3'-propylacetophenone

Product 1

HCID 133891711-(5-Bromo-2,4-dihydroxy-3-propylphenyl)ethan-1-oneYield 74%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent2×

Procedure

To a cold suspension (7°) of 5 g (0.026 mol) of 1-(2,4-dihydroxy-3-propylphenyl)ethanone in 150 ml of chloroform was added 27 ml (0.027 mol) of 1M bromine in chloroform dropwise. The mixture was stirred at 5° for 45 minutes and solvent was removed in vacuo. The residue was extracted with hot hexane and the hexane extract was boiled down to 50 ml and allowed to crystallize. Filtration gave 5.2 g, melting point 67° (74% yield) of 1-(5-bromo-2,4-dihydroxy-3-propylphenyl)ethanone.

Workup

  1. customsolvent was removed in vacuo
  2. extractionThe residue was extracted with hot hexane
  3. extractionthe hexane extract
  4. customto crystallize
  5. filtrationFiltration

Sources & evidence

ORD record
ord-1548adcbe4d54c1e95bfa5a0d4e8b801
Source dataset
uspto-grants-1988_11
Patent number
US04782176

Reaction notes

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