Triethylamine → 3,4,5-Trifluoro-4'-butoxytolan

HRID 4873

Reaction equation

HRID 4873 reaction equation
[CH2:1]([O:5][C:6]1[CH:11]=[CH:10][C:9]([C:12]#[CH:13])=[CH:8][CH:7]=1)[CH2:2][CH2:3][CH3:4].[F:14][C:15]1[CH:16]=[C:17](Br)[CH:18]=[C:19]([F:22])[C:20]=1[F:21].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:14][C:15]1[CH:16]=[C:17]([C:13]#[C:12][C:9]2[CH:8]=[CH:7][C:6]([O:5][CH2:1][CH2:2][CH2:3][CH3:4])=[CH:11][CH:10]=2)[CH:18]=[C:19]([F:22])[C:20]=1[F:21]

Participants

7

Reactant 3

HCID 8471TriethylamineHCID 6114091-Bromo-3,4,5-trifluorobenzeneHCID 27751201-Butoxy-4-ethynylbenzene

Product 1

HCID 678580313,4,5-Trifluoro-4'-butoxytolan

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-butoxyphenylacetylene, 0.02 m of 3,4,5-trifluorobromobenzene and 50 ml of triethylamine. The reaction mixture is stirred at room temperature for 2 hours, diluted with methyl tert.-butyl ether and filtered with suction, and the solution is evaporated. Purification by chromatography and/or crystallization gives 3,4,5-trifluoro-4'-butoxytolan.

Workup

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

Sources & evidence

ORD record
ord-f7a7c59d4cda43ec8f4e943cd1b919d7
Source dataset
uspto-grants-1993_09
Patent number
US05242618

Linked notes

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