1,2-Dibromoethane → 1-[4-(2-Bromoethoxy)-3-(tert-butyl)-5-nitrophenyl]-1-ethanone

HRID 1295944Notes

Reaction equation

HRID 1295944 reaction equation
C(=O)([O-])[O-].[K+].[K+].[Br:7][CH2:8][CH2:9]Br.[C:11]([C:15]1[CH:16]=[C:17]([C:25](=[O:27])[CH3:26])[CH:18]=[C:19]([N+:22]([O-:24])=[O:23])[C:20]=1[OH:21])([CH3:14])([CH3:13])[CH3:12].C(OCC)(=O)C>CN(C)C=O>[Br:7][CH2:8][CH2:9][O:21][C:20]1[C:19]([N+:22]([O-:24])=[O:23])=[CH:18][C:17]([C:25](=[O:27])[CH3:26])=[CH:16][C:15]=1[C:11]([CH3:14])([CH3:13])[CH3:12]

Participants

6

Reactant 4

HCID 78391,2-DibromoethaneHCID 8857Ethyl AcetateHCID 11430Potassium CarbonateHCID 229297281-[3-(Tert-butyl)-4-hydroxy-5-nitrophenyl]-1-ethanone

Product 1

HCID 229296701-[4-(2-Bromoethoxy)-3-(tert-butyl)-5-nitrophenyl]-1-ethanoneYield 69.8%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Potassium carbonate (4.65 g, 33.7 mmol) and 1,2-dibromoethane (31.7 g, 166.6 mmol) were added to a solution of 1-[3-(tert-butyl)-4-hydroxy-5-nitrophenyl]-1-ethanone (8.0 g, 33.7 mmol) in dimethylformamide (200 ml) and the mixture was stirred at room temperature for 12 hours. Ethyl acetate was added, the reaction mixture was washed with water and brine in that order and the organic layer was dried over anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure and the residue was purified by silica gel column chromatography (solvent: n-hexane-ethyl acetate) to yield 1-[4-(2-bromoethoxy)-3-(tert-butyl)-5-nitrophenyl]-1-ethanone (8.1 g).

Workup

  1. washthe reaction mixture was washed with water and brine in that order
  2. dry with materialthe organic layer was dried over anhydrous magnesium sulfate
  3. distillationThe solvent was distilled off under reduced pressure
  4. customthe residue was purified by silica gel column chromatography (solvent: n-hexane-ethyl acetate)

Sources & evidence

ORD record
ord-61e43feaafaa413aa50c4c690d6ee472
Source dataset
uspto-grants-2007_07
Patent number
US07244730B2

Reaction notes

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