Water → 5-Bromo-2-(4-methoxyphenyl)benzofuran

HRID 1836011Notes

Reaction equation

HRID 1836011 reaction equation
[Br: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>[Br: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 109245324-Bromo-2-iodophenol

Product 1

HCID 101495715-Bromo-2-(4-methoxyphenyl)benzofuranYield 45%

Reagents, catalysts & solvents 2

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

Procedure

A solution of 4-Bromo-2-Iodophenol [207115-22-8] (0.9 g, 3.0 mmol), 4-Methoxyphenylacetylene (0.43 g, 3.3 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 and concentrated to give a solid which was triturated with MeOH, filtered to give a solid (0.4 g, 45%): Mp=192-194° C.; 1H NMR (CDCl3) δ 7.77 (d, 2 H, J=9.1 Hz), 7.66 (s, 1 H), 7.37-7.32 (m, 2 H), 6.98 (d, 2 H, J=9.1 Hz), 6.82 (d, 1 H, J=0.8 Hz), 3.87 (s, 3 H).

Workup

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

Sources & evidence

ORD record
ord-5abadcf43b9b4721814f0aaf1f7acbe4
Source dataset
uspto-grants-2004_08
Patent number
US06774248B2

Reaction notes

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