Water → 5-tert-Butyl-2-(4-methoxy-phenyl)-benzofuran

HRID 1836014Notes

Reaction equation

HRID 1836014 reaction equation
[C:1]([C:5]1[CH:10]=[CH:9][C:8]([OH:11])=[C:7](I)[CH:6]=1)([CH3:4])([CH3:3])[CH3:2].[CH3:13][O:14][C:15]1[CH:20]=[CH:19][C:18]([C:21]#[CH:22])=[CH:17][CH:16]=1.O>CN(C=O)C.C(NCC)C.[Cu]I>[C:1]([C:5]1[CH:10]=[CH:9][C:8]2[O:11][C:21]([C:18]3[CH:19]=[CH:20][C:15]([O:14][CH3:13])=[CH:16][CH:17]=3)=[CH:22][C:7]=2[CH:6]=1)([CH3:4])([CH3:3])[CH3:2]

Participants

6

Reactant 3

HCID 962WaterHCID 2510201-Ethynyl-4-methoxybenzeneHCID 101715904-Tert-butyl-2-iodophenol

Product 1

HCID 101716205-tert-Butyl-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 4-t-butyl-2-iodophenol [38941-98-9] (1.0 g, 3.6 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, concentrated to give a solid which was triturated with MeOH, filtered to give 84 as a solid.

Workup

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

Sources & evidence

ORD record
ord-151629b1d9b4466aba734e2b335c993f
Source dataset
uspto-grants-2004_08
Patent number
US06774248B2

Reaction notes

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