Ethanol → Ethyl 3-bromofuran-2-carboxylate

HRID 2109370Notes

Reaction equation

HRID 2109370 reaction equation
[CH3:1][CH2:2]N=C=NCCCN(C)C.C(O)C.[Br:15][C:16]1[CH:20]=[CH:19][O:18][C:17]=1[C:21]([OH:23])=[O:22]>CN(C)C1C=CN=CC=1.ClCCl>[Br:15][C:16]1[CH:20]=[CH:19][O:18][C:17]=1[C:21]([O:23][CH2:1][CH3:2])=[O:22]

Participants

6

Reactant 3

HCID 702EthanolHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 6054793-Bromofuran-2-carboxylic acid

Product 1

HCID 22456149Ethyl 3-bromofuran-2-carboxylateYield 88.7%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Conditions

Temperature
25 °C

Procedure

WSC (17.3 g), 4-dimethylaminopyridine (1.1 g) and ethanol (5.2 ml) were added to a dichloromethane solution (100 ml) of 17.2 g 3-bromo-2-furancarboxylic acid and stirred for 5 hours at 25° C. The reaction solution was washed with saturated brine and dried over MgSO4. The solvent was evaporated under reduced pressure, and the residue was purified by silica gel column chromatography (eluent: ethyl acetate/hexane=1/30), thereby giving 17.5 g of the desired compound.

Workup

  1. washThe reaction solution was washed with saturated brine
  2. dry with materialdried over MgSO4
  3. customThe solvent was evaporated under reduced pressure
  4. customthe residue was purified by silica gel column chromatography (eluent: ethyl acetate/hexane=1/30)

Sources & evidence

ORD record
ord-ddc637a82b044fd18af0bc4b6bec9674
Source dataset
uspto-grants-2009_04
Patent number
US07514452B2

Reaction notes

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