Hydrochloric Acid → HCID 18960035, compound

HRID 1707900Notes

Reaction equation

HRID 1707900 reaction equation
Br[C:2]1[C:7]([F:8])=[CH:6][C:5]([C:9]#[C:10][C:11]2[CH:16]=[CH:15][C:14]([CH2:17][CH2:18][CH3:19])=[CH:13][CH:12]=2)=[C:4]([F:20])[CH:3]=1.[CH2:21]([C:24]1[CH:29]=[CH:28][C:27]([C:30]#[CH:31])=[CH:26][CH:25]=1)[CH2:22][CH3:23].Cl>C(N(CC)CC)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.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>[CH2:17]([C:14]1[CH:15]=[CH:16][C:11]([C:10]#[C:9][C:5]2[CH:6]=[C:7]([F:8])[C:2]([C:31]#[C:30][C:27]3[CH:28]=[CH:29][C:24]([CH2:21][CH2:22][CH3:23])=[CH:25][CH:26]=3)=[CH:3][C:4]=2[F:20])=[CH:12][CH:13]=1)[CH2:18][CH3:19]

Participants

8

Reactant 3

HCID 313Hydrochloric AcidHCID 27751331-Ethynyl-4-propylbenzeneHCID 67742269HCID 67742269, compound

Product 1

HCID 18960035HCID 18960035, compoundYield 44.8%

Reagents, catalysts & solvents 4

HCID 11776TriphenylphosphineCatalystHCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 178418476HCID 178418476, compoundCatalystHCID 8471TriethylamineSolvent

Procedure

4-Bromo-2,5-difluoro-4'-propyltolane (5.0 g), 4-propylphenylacetylene (2.1 g), triphenylphosphine (0.06 g) and bis(triphenylphosphine)palladium(II) chloride (0.04 g) were dissolved in triethylamine (33 ml) under nitrogen atmosphere, and then copper(I) iodide (0.01 g) was added thereto, followed by refluxing for 5 hours. The reaction solution was poured into a mixture of concentrated hydrochloric acid (16 ml) and ice (30 g), and then extracted with chloroform. After washing the resultant with water twice, chloroform was distilled off therefrom. The residue was purified using silica gel-chloroform column chromatography, and then recrystallized from acetone to give 1,4-bis(4'-propylphenylethynyl)-2,5-difluorobenzene (2.6 g). The C-N point and the N-I point of the compound were 153.4° C. and 197.7° C., respectively.

Workup

  1. temperatureby refluxing for 5 hours
  2. extractionextracted with chloroform
  3. washAfter washing the resultant with water twice
  4. distillationchloroform was distilled off
  5. customThe residue was purified
  6. customrecrystallized from acetone

Sources & evidence

ORD record
ord-566e4f1655174cd4b27709f5edef5295
Source dataset
uspto-grants-1994_10
Patent number
US05356558

Reaction notes

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