Sodium Carbonate → Ethyl 5-bromofuran-3-carboxylate

HRID 537060

Reaction equation

HRID 537060 reaction equation
[O:1]1[CH:5]=[CH:4][C:3]([C:6]([O:8][CH2:9][CH3:10])=[O:7])=[CH:2]1.[Br:11]Br.C([O-])([O-])=O.[Na+].[Na+]>C(Cl)(Cl)Cl>[Br:11][C:5]1[O:1][CH:2]=[C:3]([C:6]([O:8][CH2:9][CH3:10])=[O:7])[CH:4]=1

Participants

5

Reactant 3

HCID 10340Sodium CarbonateHCID 24408BromineHCID 69201Ethyl 3-furoate

Product 1

HCID 14592142Ethyl 5-bromofuran-3-carboxylateYield 53.3%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent2×

Procedure

To a solution of ethyl 3-furoate (50.0 g, 360 mmol) in chloroform (380 mL) was added bromine (56.0 g, 360 mmol) in chloroform. The reaction mixture was allowed to stir at rt overnight and then poured into 10% aqueous Na2CO3. The mixture was extracted with DCM. The organic solutions were combined and washed with water until pH=7. The organic solution was concentrated and then distilled to give ethyl 5-bromo-3-furoate (42 g, 40%).

Workup

  1. extractionThe mixture was extracted with DCM
  2. washwashed with water until pH=7
  3. concentrationThe organic solution was concentrated
  4. distillationdistilled

Sources & evidence

ORD record
ord-7406ec14cb494712806516432f970ee3
Source dataset
uspto-grants-2014_10
Patent number
US08859768B2

Linked notes

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