5-Bromo-7-fluoro-1-benzofuran-2-carboxylic acid → 5-Bromo-7-fluorobenzofuran

HRID 2405382Notes

Reaction equation

HRID 2405382 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([F:14])[C:5]2[O:9][C:8](C(O)=O)=[CH:7][C:6]=2[CH:13]=1>N1C2C(=CC=CC=2)C=CC=1.[Cu]>[Br:1][C:2]1[CH:3]=[C:4]([F:14])[C:5]2[O:9][CH:8]=[CH:7][C:6]=2[CH:13]=1

Participants

4

Reactant 1

HCID 623792185-Bromo-7-fluoro-1-benzofuran-2-carboxylic acid

Product 1

HCID 221448205-Bromo-7-fluorobenzofuranYield 102.2%

Reagents, catalysts & solvents 2

HCID 23978CopperCatalystHCID 7047QuinolineSolvent

Procedure

A solution of 5-bromo-7-fluoro-1-benzofuran-2-carboxylic acid (1.274 mmol) in quinoline (2 mL) was treated with copper dust (0.236 mmol). The reaction was purged with nitrogen, sealed and irradiated in a microwave reactor at 230° C. for 60 min. The solution was diluted with ethyl acetate and was filtered through Celite. The filtrate was concentrated in vacuo, and the residue was purified by flash chromatography (hexanes) to provide the title compound as a clear oil (280 mg, 100% yield). 1H NMR (400 MHz, DMSO-d6) δ ppm 8.17 (d, J=2.02 Hz, 1H) 7.77 (d, J=1.77 Hz, 1H) 7.55 (dd, J=10.48, 1.64 Hz, 1H) 7.07 (dd, J=3.16, 2.15 Hz, 1H).

Workup

  1. customThe reaction was purged with nitrogen
  2. customsealed
  3. customirradiated in a microwave reactor at 230° C. for 60 min
  4. additionThe solution was diluted with ethyl acetate
  5. filtrationwas filtered through Celite
  6. concentrationThe filtrate was concentrated in vacuo
  7. customthe residue was purified by flash chromatography (hexanes)

Sources & evidence

ORD record
ord-10f1d137e3c64bb3baf7368d1f2ee6cd
Source dataset
uspto-grants-2014_08
Patent number
US08802864B2

Reaction notes

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