Ethyl bromoacetate → Ethyl (2-hydroxy-4-nitrophenoxy)acetate

HRID 1106888Notes

Reaction equation

HRID 1106888 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]([OH:11])[C:7](=[CH:9][CH:10]=1)[OH:8])([O-:3])=[O:2].C(=O)([O-])[O-].[K+].[K+].Br[CH2:19][C:20]([O:22][CH2:23][CH3:24])=[O:21]>CN(C=O)C>[OH:11][C:6]1[CH:5]=[C:4]([N+:1]([O-:3])=[O:2])[CH:10]=[CH:9][C:7]=1[O:8][CH2:19][C:20]([O:22][CH2:23][CH3:24])=[O:21]

Participants

5

Reactant 3

HCID 7748Ethyl bromoacetateHCID 11430Potassium CarbonateHCID 35051094-Nitrocatechol

Product 1

HCID 54480905Ethyl (2-hydroxy-4-nitrophenoxy)acetate

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
72.5 °C

Procedure

4-Nitrocatechol (5 g, 32.2 mmol) was dissolved in DMF (50 ml); thereafter, potassium carbonate (8.9 g, 64.5 mmol) was added and with heating at 70-75° C., ethyl bromoacetate (7.18 ml) was slowly added dropwise, followed by stirring at the same temperature for 15 min. The reaction solution was cooled to room temperature and filtered; after being concentrated under vacuum, the filtrate was diluted with a saturated aqueous solution of sodium bicarbonate (50 ml) and subjected to extraction with ethyl acetate (300 ml). The extracted organic layer was dried with magnesium sulfate and the solvent was evaporated. The resulting residue was purified by being subjected to column chromatography on silica gel using a 2:1 solvent system of n-hexane and ethyl acetate as an eluent. The fractions containing the product were collected and the solvent was evaporated to yield the end compound ethyl (2-hydroxy-4-nitrophenoxy)acetate (1.05 g).

Workup

  1. temperatureThe reaction solution was cooled to room temperature
  2. filtrationfiltered
  3. concentrationafter being concentrated under vacuum
  4. additionthe filtrate was diluted with a saturated aqueous solution of sodium bicarbonate (50 ml)
  5. extractionsubjected to extraction with ethyl acetate (300 ml)
  6. dry with materialThe extracted organic layer was dried with magnesium sulfate
  7. customthe solvent was evaporated
  8. customThe resulting residue was purified
  9. additionThe fractions containing the product
  10. customwere collected
  11. customthe solvent was evaporated

Sources & evidence

ORD record
ord-76bc2f146b0c4cb89f54a2957dfeaac1
Source dataset
uspto-grants-2000_05
Patent number
US06057358

Reaction notes

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