Ethyl bromoacetate → ethyl 2-(4-formyl-2-nitrophenoxy)acetate

HRID 1271678Notes

Reaction equation

HRID 1271678 reaction equation
[OH:1][C:2]1[CH:9]=[CH:8][C:5]([CH:6]=[O:7])=[CH:4][C:3]=1[N+:10]([O-:12])=[O:11].Br[CH2:14][C:15]([O:17][CH2:18][CH3:19])=[O:16].C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O>[CH2:18]([O:17][C:15](=[O:16])[CH2:14][O:1][C:2]1[CH:9]=[CH:8][C:5]([CH:6]=[O:7])=[CH:4][C:3]=1[N+:10]([O-:12])=[O:11])[CH3:19]

Participants

5

Reactant 3

HCID 7748Ethyl bromoacetateHCID 11430Potassium CarbonateHCID 181694-Hydroxy-3-nitrobenzaldehyde

Product 1

HCID 5305379ethyl 2-(4-formyl-2-nitrophenoxy)acetate

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
60 °C

Procedure

A solution of 4-hydroxy-3-nitro-benzaldehyde (6.9 g) and ethyl bromoacetate (5.0 ml) in dimethylformamide (250 ml) was treated with anhydrous potassium carbonate (10 g) and the mixture was heated at 60° C. for 18 hours and evaporated to dryness. The residue was partitioned between water and ether, and the ether layer was washed with 0.5M sodium hydroxide, dried over anhydrous sodium sulphate and evaporated to give an oil that was chromatographed on silica gel (ethyl acetate/dichloromethane) to afford an oil (1.9 g)

Workup

  1. customevaporated to dryness
  2. customThe residue was partitioned between water and ether
  3. washthe ether layer was washed with 0.5M sodium hydroxide
  4. dry with materialdried over anhydrous sodium sulphate
  5. customevaporated
  6. customto give an oil that
  7. customwas chromatographed on silica gel (ethyl acetate/dichloromethane)

Sources & evidence

ORD record
ord-e9fa6cc2bdd7468d91bb4821e6668ea7
Source dataset
uspto-grants-2007_04
Patent number
US07205408B2

Reaction notes

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