Ethyl bromoacetate → HCID 12212162, compound

HRID 1993900Notes

Reaction equation

HRID 1993900 reaction equation
[Br:1][C:2]1[CH:8]=[CH:7][C:5]([NH2:6])=[CH:4][C:3]=1[Cl:9].C(=O)([O-])[O-].[Na+].[Na+].Br[CH2:17][C:18]([O:20][CH2:21][CH3:22])=[O:19]>C(O)C.CCOCC>[CH2:21]([O:20][C:18](=[O:19])[CH2:17][NH:6][C:5]1[CH:7]=[CH:8][C:2]([Br:1])=[C:3]([Cl:9])[CH:4]=1)[CH3:22]

Participants

6

Reactant 3

HCID 7748Ethyl bromoacetateHCID 10340Sodium CarbonateHCID 888884-Bromo-3-chloroaniline

Product 1

HCID 12212162HCID 12212162, compoundYield 62%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 3283Diethyl EtherSolvent

Procedure

To a solution of 4-bromo-3-chloro-aniline (0.64 g, 3.10 mmol) in ethanol (7 ml) were added sodium carbonate (0.49 g, 4.65 mmol) and ethyl bromoacetate (0.38 ml, 3.41 mmol). The resulting suspension was stirred at room temperature for 10 min and was then heated at 100° C. for 30 min under microwave irradiation. The mixture was then cooled to room temperature, diluted with ether, and filtered. The filtrate was washed with 1 M aqueous hydrochloric acid, the phases separated, and the aqueous phase extracted with ether. The combined organic extracts were dried over sodium sulphate, filtered and concentrated in vacuo. The residue was purified by flash chromatography (SiO2: heptane/ethyl acetate=gradient 100:0-70:30) to yield a brown oil (0.56 g, 62%); MS (ISP): 296.1, 294.1, 292.1 ([M+H]+.).

Workup

  1. temperaturewas then heated at 100° C. for 30 min under microwave irradiation
  2. temperatureThe mixture was then cooled to room temperature
  3. filtrationfiltered
  4. washThe filtrate was washed with 1 M aqueous hydrochloric acid
  5. customthe phases separated
  6. extractionthe aqueous phase extracted with ether
  7. dry with materialThe combined organic extracts were dried over sodium sulphate
  8. filtrationfiltered
  9. concentrationconcentrated in vacuo
  10. customThe residue was purified by flash chromatography (SiO2: heptane/ethyl acetate=gradient 100:0-70:30)

Sources & evidence

ORD record
ord-ad1acba1085e41b0a6b2806b39774ab9
Source dataset
uspto-grants-2010_01
Patent number
US07652055B2

Reaction notes

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