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

HRID 723506Notes

Reaction equation

HRID 723506 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 diethyl ether, and the diethyl ether layer was washed with 0.5M sodium hydroxide. It was then dried over anhydrous sodium sulfate 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 diethyl ether
  3. washthe diethyl ether layer was washed with 0.5M sodium hydroxide
  4. dry with materialIt was then dried over anhydrous sodium sulfate
  5. customevaporated
  6. customto give an oil that
  7. customwas chromatographed on silica gel (ethyl acetate/dichloromethane)

Sources & evidence

ORD record
ord-d8e5901b8f764d2280e337ae273e9c18
Source dataset
uspto-grants-2006_11
Patent number
US07141564B2

Reaction notes

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