Triethylamine → 3,4-Difluoro-4'-ethoxytolan

HRID 4872

Reaction equation

HRID 4872 reaction equation
[CH2:1]([O:3][C:4]1[CH:9]=[CH:8][C:7]([C:10]#[CH:11])=[CH:6][CH:5]=1)[CH3:2].[F:12][C:13]1[CH:14]=[C:15](I)[CH:16]=[CH:17][C:18]=1[F:19].C(N(CC)CC)C>C(OC)(C)(C)C.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.[Cu]I>[F:12][C:13]1[CH:14]=[C:15]([C:11]#[C:10][C:7]2[CH:8]=[CH:9][C:4]([O:3][CH2:1][CH3:2])=[CH:5][CH:6]=2)[CH:16]=[CH:17][C:18]=1[F:19]

Participants

7

Reactant 3

HCID 8471TriethylamineHCID 27244441,2-Difluoro-4-iodobenzeneHCID 27751241-Ethoxy-4-ethynylbenzene

Product 1

HCID 678579873,4-Difluoro-4'-ethoxytolan

Reagents, catalysts & solvents 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 178418476HCID 178418476, compoundCatalystHCID 15413tert-Butyl methyl etherSolvent

Procedure

0.4 mmol of bis(triphenylphosphine)palladium(II) chloride and 0.2 mmol of CuI are added at room temperature to a mixture of 0.02 m of 4-ethoxyphenylacetylene, 0.02 m of 3,4-difluoroiodobenzene and 50 ml of triethylamine. The reaction mixture is stirred at room temperature for 2 hours, diluted with 100 ml of methyl tert.-butyl ether and filtered with suction, and the solution is evaporated. Purification by chromatography and/or crystallization gives 3,4-difluoro-4'-ethoxytolan, K 67 I, Δε=11.18.

Workup

  1. filtrationfiltered with suction
  2. customthe solution is evaporated
  3. customPurification
  4. customby chromatography and/or crystallization

Sources & evidence

ORD record
ord-c11e140ba9cd45de8bbf75d1cbd64d0a
Source dataset
uspto-grants-1993_09
Patent number
US05242618

Linked notes

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