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

HRID 1794512Notes

Reaction equation

HRID 1794512 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([Cl: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>[Cl:8][C:6]1[CH:7]=[C:2]([Cl: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

5

Reactant 3

HCID 962WaterHCID 2510201-Ethynyl-4-methoxybenzeneHCID 45590102,4-Dichloro-6-iodophenol

Product 1

HCID 101254875,7-Dichloro-2-(4-methoxy-phenyl)-benzofuranYield 42%

Reagents, catalysts & solvents 1

HCID 86589549DMF DiethylamineSolvent

Procedure

A solution of 2,4-Dichloro-6-iodo-phenol [2040-83-7] (2.0 g, 6.9 mmol), 4-Methoxyphenylacetylene (0.91 g, 6.9 mmol), PdCl2P(PH3)2 (0.15 g), and Cul (50 mg) in DMF/Diethylamine (26 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, filtered to give 85 as a solid (0.80 g, 42%): Mp=1.72–174° C.; 1H NMR (CDCl3) δ 7.82 (d, 2 H, J=8.1 Hz), 7.41 (d, 1 H, J=1.8 Hz), 7.24 (d, 1 H, J=1.9 Hz), 7.00 (d, 2 H, J=8.8 Hz), 6.84 (s, 3 H), 3.87 (s, 3 H); MS 293/295 [M+H]+

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-4896345775604456a2c55114f908879b
Source dataset
uspto-grants-2006_04
Patent number
US07022733B2

Reaction notes

Loading…