Triethylamine → Methyl 4-[(4-ethoxyphenyl)ethynyl]-2-fluorobenzoate

HRID 1888736Notes

Reaction equation

HRID 1888736 reaction equation
Br[C:2]1[CH:11]=[CH:10][C:5]([C:6]([O:8][CH3:9])=[O:7])=[C:4]([F:12])[CH:3]=1.C(N(CC)CC)C.[CH2:20]([O:22][C:23]1[CH:28]=[CH:27][C:26]([C:29]#[CH:30])=[CH:25][CH:24]=1)[CH3:21]>C1COCC1.C(OCC)(=O)C.[Cu]I.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[CH2:20]([O:22][C:23]1[CH:28]=[CH:27][C:26]([C:29]#[C:30][C:2]2[CH:11]=[CH:10][C:5]([C:6]([O:8][CH3:9])=[O:7])=[C:4]([F:12])[CH:3]=2)=[CH:25][CH:24]=1)[CH3:21]

Participants

8

Reactant 3

HCID 8471TriethylamineHCID 27751241-Ethoxy-4-ethynylbenzeneHCID 113453114-Bromo-2-fluoro-benzoic acid methyl ester

Product 1

HCID 58047371Methyl 4-[(4-ethoxyphenyl)ethynyl]-2-fluorobenzoateYield 84%

Reagents, catalysts & solvents 4

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 178418476HCID 178418476, compoundCatalystHCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

To methyl 4-bromo-2-fluorobenzoate (1.29 g, 5.54 mmol) in THF (10 mL)-triethylamine (5 mL) solvent were added 1-ethoxy-4-ethynylbenzene (1.24 mL, 8.30 mmol), copper(I) iodide (106 mg, 0.544 mmol) and bis(triphenylphosphine)palladium(II) chloride (195 mg, 0.277 mmol), and the mixture was stirred under an argon stream at room temperature for 15 min. The reaction mixture was diluted with ethyl acetate, and the mixture was washed with water, and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure and the obtained residue was purified by silica gel column chromatography (hexane:ethyl acetate=97:3 to 17:3) to give the title compound (1.38 g, yield 84%) as an oil.

Workup

  1. washthe mixture was washed with water
  2. dry with materialdried over anhydrous magnesium sulfate
  3. customThe solvent was evaporated under reduced pressure
  4. customthe obtained residue was purified by silica gel column chromatography (hexane:ethyl acetate=97:3 to 17:3)

Sources & evidence

ORD record
ord-e9232c57cf274ac2bb016a619f1a5400
Source dataset
uspto-grants-2013_08
Patent number
US08501804B2

Reaction notes

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