Water → 5,7-Difluoro-2-(4-methoxy-phenyl)-benzofuran

HRID 1836016Notes

Reaction equation

HRID 1836016 reaction equation
[F:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[C:4](I)[C:3]=1[OH:10].[CH3:11][O:12][C:13]1[CH:18]=[CH:17][C:16]([C:19]#[CH:20])=[CH:15][CH:14]=1.O>CN(C=O)C.C(NCC)C.[Cu]I>[F:8][C:6]1[CH:7]=[C:2]([F:1])[C:3]2[O:10][C:19]([C:16]3[CH:17]=[CH:18][C:13]([O:12][CH3:11])=[CH:14][CH:15]=3)=[CH:20][C:4]=2[CH:5]=1

Participants

6

Reactant 3

HCID 962WaterHCID 2510201-Ethynyl-4-methoxybenzeneHCID 222216242,4-Difluoro-6-iodophenol

Product 1

HCID 102860365,7-Difluoro-2-(4-methoxy-phenyl)-benzofuran

Reagents, catalysts & solvents 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 86589549DMF DiethylamineSolvent

Procedure

A solution of 2,4-Difluoro-6-iodo-phenol (1.0 g, 3.9 mmol), 4-Methoxyphenylacetylene(0.53 g, 4.0 mmol), PdCl2P(PH3)2 (70 mg), and CuI (50 mg) in DMF/Diethylamine (10 ml) was heated to 60° C. After 1 hr, the reaction was cooled and poured into water which was extracted with EtOAc. The organic layer was dried over MgSO4, filtered and concentrated to give a solid which was triturated with MeOH and filtered to give 86 as a solid.

Workup

  1. temperaturethe reaction was cooled
  2. extractionwas extracted with EtOAc
  3. dry with materialThe organic layer was dried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customto give a solid which
  7. customwas triturated with MeOH
  8. filtrationfiltered

Sources & evidence

ORD record
ord-15f1ce97aa4246738fbb56873cc20be3
Source dataset
uspto-grants-2004_08
Patent number
US06774248B2

Reaction notes

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