5-Chloro-1-benzofuran-2-carboxylic acid → 5-Chloro-1-benzofuran

HRID 2110056Notes

Reaction equation

HRID 2110056 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[O:9][C:8](C(O)=O)=[CH:7][C:6]=2[CH:13]=1>CN1CCCC1=O.[Cu]>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[O:9][CH:8]=[CH:7][C:6]=2[CH:13]=1

Participants

4

Reactant 1

HCID 9378385-Chloro-1-benzofuran-2-carboxylic acid

Product 1

HCID 900135-Chloro-1-benzofuranYield 418.7%

Reagents, catalysts & solvents 2

HCID 23978CopperCatalystHCID 13387N-methyl-2-pyrrolidoneSolvent

Conditions

Temperature
250 °C

Procedure

To a solution of 5-chloro-1-benzofuran-2-carboxylic acid (0.2 g) in 1-methyl-2-pyrrolidinone (2 ml) was added copper granules (0.2 g). The reaction mixture was heated at 250° C. for 3.5 min in a microwave. The reaction vessel was cooled to room temperature and the mixture combined with four other similar mixtures and the combined mixtures partitioned between water and diethyl ether. The organic layer was washed with water and brine, dried (over magnesium sulphate) and concentrated under reduced pressure to give the title compound (0.65 g) as a yellow oil.

Workup

  1. temperatureThe reaction vessel was cooled to room temperature
  2. customthe combined mixtures partitioned between water and diethyl ether
  3. washThe organic layer was washed with water and brine
  4. dry with materialdried (over magnesium sulphate)
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-4f5c187b1bf6448986b35f2d2606fee2
Source dataset
uspto-grants-2009_04
Patent number
US07517879B2

Reaction notes

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