Sodium Carbonate → Ethyl 5-bromo-4-(3-chlorophenyl)furan-2-carboxylate

HRID 2190123Notes

Reaction equation

HRID 2190123 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([C:8]2[CH:9]=[C:10]([C:13]([O:15][CH2:16][CH3:17])=[O:14])[O:11][CH:12]=2)[CH:5]=[CH:6][CH:7]=1.[Br:18]Br.C(=O)([O-])[O-].[Na+].[Na+]>C(O)(=O)C>[Br:18][C:12]1[O:11][C:10]([C:13]([O:15][CH2:16][CH3:17])=[O:14])=[CH:9][C:8]=1[C:4]1[CH:5]=[CH:6][CH:7]=[C:2]([Cl:1])[CH:3]=1

Participants

5

Reactant 3

HCID 10340Sodium CarbonateHCID 24408BromineHCID 58064785Ethyl 4-(3-chlorophenyl)furan-2-carboxylate

Product 1

HCID 58064768Ethyl 5-bromo-4-(3-chlorophenyl)furan-2-carboxylate

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
60 °C

Procedure

0.82 g (3.27 mmol) of the compound from Example 9A are provided in 21 ml of acetic acid, 0.17 ml (3.27 mmol) of bromine are added and the mixture is stirred at 60° C. overnight. A saturated aqueous sodium carbonate solution is added carefully, and the mixture is extracted with ethyl acetate. The organic phase is washed twice with water, dried over sodium sulfate, filtered and concentrated. The crude product is purified by flash chromatography (mobile phase: cyclohexane/ethyl acetate 40:1). 1.05 g (91% of theory) of the title compound are obtained.

Workup

  1. extractionthe mixture is extracted with ethyl acetate
  2. washThe organic phase is washed twice with water
  3. dry with materialdried over sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe crude product is purified by flash chromatography (mobile phase: cyclohexane/ethyl acetate 40:1)

Sources & evidence

ORD record
ord-1a83798df0a747d88e9372c772f53b1f
Source dataset
uspto-grants-2012_12
Patent number
US08324268B2

Reaction notes

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