Water → HCID 10285960, compound

HRID 1836013Notes

Reaction equation

HRID 1836013 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([OH:8])=[C:4](I)[CH:3]=1.[CH3:10][O:11][C:12]1[CH:17]=[CH:16][C:15]([C:18]#[CH:19])=[CH:14][CH:13]=1.O>CN(C=O)C.C(NCC)C.[Cu]I>[F:1][C:2]1[CH:7]=[CH:6][C:5]2[O:8][C:18]([C:15]3[CH:16]=[CH:17][C:12]([O:11][CH3:10])=[CH:13][CH:14]=3)=[CH:19][C:4]=2[CH:3]=1

Participants

6

Reactant 3

HCID 962WaterHCID 2510201-Ethynyl-4-methoxybenzeneHCID 101714174-Fluoro-2-iodophenol

Product 1

HCID 10285960HCID 10285960, compound

Reagents, catalysts & solvents 2

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

Procedure

A solution of 4-Fluoro-2-Iodophenol [2713-29-3] (0.9 g, 3.8 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 83 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-86bc394c8bed4da79fbb1eb646f523e5
Source dataset
uspto-grants-2004_08
Patent number
US06774248B2

Reaction notes

Loading…