Dimethylformamide → Methyl 2-phenylbenzofuran-5-carboxylate

HRID 1827976Notes

Reaction equation

HRID 1827976 reaction equation
I[C:2]1[CH:3]=[C:4]([CH:9]=[CH:10][C:11]=1[OH:12])[C:5]([O:7][CH3:8])=[O:6].[C:13]1([C:19]#[CH:20])[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.CN(C)C(=N)N(C)C.CN(C=O)C>[Cu]I.O>[CH3:8][O:7][C:5]([C:4]1[CH:9]=[CH:10][C:11]2[O:12][C:19]([C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=3)=[CH:20][C:2]=2[CH:3]=1)=[O:6]

Participants

7

Reactant 4

HCID 6228DimethylformamideHCID 10821PhenylacetyleneHCID 664601,1,3,3-TetramethylguanidineHCID 11346465Methyl 4-hydroxy-3-iodobenzoate

Product 1

HCID 66865443Methyl 2-phenylbenzofuran-5-carboxylateYield 99.1%

Reagents, catalysts & solvents 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 962WaterSolvent

Procedure

A mixture of methyl 3-iodo-4-hydroxybenzoate 26 (1 g, 3.6 mmol), phenylacetylene (2 ml, 18 mmol), tetramethylguanidine (4.5 ml, 36 mmol), copper(I)iodide (34 mg, 1.8 mmol), bis(triphenylphosphine)palladium (II)chloride (130 mg, 1.8 mmol) and DMF (20 ml) was stirred at room temperature overnight. The reaction mixture was poured into water, extracted, washed and dried. After evaporation of the solvent, the residue was purified by chromatography to give about 0.9 g of 2-phenyl-benzofuran-5-carboxylic acid methyl ester 27.

Workup

  1. extractionextracted
  2. washwashed
  3. customdried
  4. customAfter evaporation of the solvent
  5. customthe residue was purified by chromatography

Sources & evidence

ORD record
ord-6d6c47b87e354677877e5da0b955a92b
Source dataset
uspto-grants-2006_06
Patent number
US07056903B2

Reaction notes

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