Ethyl bromoacetate → Ethyl (5-bromobenzofuran)-2-carboxylate

HRID 1916645Notes

Reaction equation

HRID 1916645 reaction equation
C([O-])([O-])=O.[Na+].[Na+].[Br:7][C:8]1[CH:15]=[C:12]([CH:13]=O)[C:11]([OH:16])=[CH:10][CH:9]=1.Br[CH2:18][C:19]([O:21][CH2:22][CH3:23])=[O:20]>CN(C=O)C.O>[Br:7][C:8]1[CH:9]=[CH:10][C:11]2[O:16][C:18]([C:19]([O:21][CH2:22][CH3:23])=[O:20])=[CH:13][C:12]=2[CH:15]=1

Participants

6

Reactant 3

HCID 7748Ethyl bromoacetateHCID 10340Sodium CarbonateHCID 728635-Bromosalicylaldehyde

Product 1

HCID 735184Ethyl (5-bromobenzofuran)-2-carboxylate

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

13.8 g (100 mmol) Na2CO3 are added to a solution of 4.02 g (20.0 mmol) 5-bromo-salicylaldehyde and 2.26 mL (20.0 mmol, 98%) ethyl bromoacetate in 50 mL DMF. The reaction mixture is heated to 80° C. and stirred for 2 h at this temperature. It is diluted with 200 mL water, the aqueous phase is extracted three times with 100 mL tert-butylmethylether and the combined organic extracts are washed twice with 50 mL water. The organic phase is dried over MgSO4, filtered through activated charcoal and the solvent is eliminated i.vac.

Workup

  1. extractionthe aqueous phase is extracted three times with 100 mL tert-butylmethylether
  2. washthe combined organic extracts are washed twice with 50 mL water
  3. dry with materialThe organic phase is dried over MgSO4
  4. filtrationfiltered through activated charcoal

Sources & evidence

ORD record
ord-af8a151465c641a1965b75762ae374e0
Source dataset
uspto-grants-2013_12
Patent number
US08618132B2

Reaction notes

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