1,2-Dibromoethane → HCID 58294044, compound

HRID 416026Notes

Reaction equation

HRID 416026 reaction equation
[Br:1][C:2]1[C:3]([OH:12])=[C:4]([C:9](=[O:11])[CH3:10])[CH:5]=[C:6]([Cl:8])[CH:7]=1.C(=O)([O-])[O-].[K+].[K+].[Br:19][CH2:20][CH2:21]Br>CN(C)C=O.O>[Br:1][C:2]1[C:3]([O:12][CH2:21][CH2:20][Br:19])=[C:4]([C:9](=[O:11])[CH3:10])[CH:5]=[C:6]([Cl:8])[CH:7]=1

Participants

6

Reactant 3

HCID 78391,2-DibromoethaneHCID 11430Potassium CarbonateHCID 27355463'-Bromo-5'-chloro-2'-hydroxyacetophenone

Product 1

HCID 58294044HCID 58294044, compoundYield 123.4%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
50 °C

Procedure

A suspension of 3′-bromo-5′-chloro-2′-hydroxyacetophenone (2.4 g, 10 mmol), potassium carbonate (2.8 g, 20 mmol) and 1,2-dibromoethane (3.5 mL, 41 mmol) in anhydrous N,N-dimethylformamide (30 mL) was stirred at 50° C. overnight. After cooling, the reaction mixture was diluted with water (100 mL), and the whole was extracted with ethyl acetate (100 mL). The organic layer was washed with saturated aqueous ammonium chloride solution (50 mL, twice) and brine (50 mL) and dried over anhydrous magnesium sulfate. The solvent was removed in vacuo to give the title reference compound (4.4 g) as orange oil (Quantitative).

Workup

  1. temperatureAfter cooling
  2. extractionthe whole was extracted with ethyl acetate (100 mL)
  3. washThe organic layer was washed with saturated aqueous ammonium chloride solution (50 mL
  4. dry with materialtwice) and brine (50 mL) and dried over anhydrous magnesium sulfate
  5. customThe solvent was removed in vacuo

Sources & evidence

ORD record
ord-ed82bdcdceb54c1598375c2f5deace5e
Source dataset
uspto-grants-2012_01
Patent number
US08088817B2

Reaction notes

Loading…