Methyl 5-bromofuran-2-carboxylate → Methyl 5-(methylsulfonyl)furan-2-carboxylate

HRID 559665Notes

Reaction equation

HRID 559665 reaction equation
[CH3:1][O:2][C:3]([C:5]1[O:6][C:7](Br)=[CH:8][CH:9]=1)=[O:4].[CH3:11][S:12]([O-:14])=[O:13].[Na+]>CS(C)=O.O.C(OCC)(=O)C.[Cu]I>[CH3:1][O:2][C:3]([C:5]1[O:6][C:7]([S:12]([CH3:11])(=[O:14])=[O:13])=[CH:8][CH:9]=1)=[O:4]

Participants

7

Reactant 2

HCID 599633Methyl 5-bromofuran-2-carboxylateHCID 2733271Sodium methanesulfinate

Product 1

HCID 53485860Methyl 5-(methylsulfonyl)furan-2-carboxylate

Reagents, catalysts & solvents 4

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 679Dimethyl SulfoxideSolventHCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
110 °C

Procedure

To a solution of 5-bromo-furan-2-carboxylic acid methyl ester (4.7 g, 23 mmol) in DMSO (25 mL) was added the sodium methanesulfinate (5.5 g, 46 mmol) followed by copper (I) iodide (4.4 g, 23 mmol). The mixture was then heated to 110° C. for 2 hours. The reaction was diluted with water (100 mL) and ethyl acetate (100 mL) and filtered through diatomaceous earth. The aqueous layer was separated and extracted with ethyl acetate (3×50 mL). The combined organic layers were washed with brine (2×50 mL), dried over sodium sulfate, filtered and concentrated to afford 5-methanesulfonyl-furan-2-carboxylic acid methyl ester.

Workup

  1. filtrationfiltered through diatomaceous earth
  2. customThe aqueous layer was separated
  3. extractionextracted with ethyl acetate (3×50 mL)
  4. washThe combined organic layers were washed with brine (2×50 mL)
  5. dry with materialdried over sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-a8d162e8f7a54e57b0395aa4d5eda98c
Source dataset
uspto-grants-2011_11
Patent number
US08063065B2

Reaction notes

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