3,4-Difluorophenylacetylene → 2-Propyl-7-(3,4-difluorophenylethynyl)phenanthrene

HRID 1830482Notes

Reaction equation

HRID 1830482 reaction equation
I[C:2]1[CH:15]=[CH:14][C:13]2[C:12]3[C:7](=[CH:8][C:9]([CH2:16][CH2:17][CH3:18])=[CH:10][CH:11]=3)[CH:6]=[CH:5][C:4]=2[CH:3]=1.[C:19]([C:21]1[CH:26]=[CH:25][C:24]([F:27])=[C:23]([F:28])[CH:22]=1)#[CH:20]>CN(C)C=O.C(N(CC)CC)C.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[CH2:16]([C:9]1[CH:10]=[CH:11][C:12]2[C:13]3[C:4](=[CH:3][C:2]([C:20]#[C:19][C:21]4[CH:26]=[CH:25][C:24]([F:27])=[C:23]([F:28])[CH:22]=4)=[CH:15][CH:14]=3)[CH:5]=[CH:6][C:7]=2[CH:8]=1)[CH2:17][CH3:18]

Participants

6

Reactant 2

HCID 138784543,4-DifluorophenylacetyleneHCID 220446942-Iodo-7-propyl-phenanthrene

Product 1

HCID 220450902-Propyl-7-(3,4-difluorophenylethynyl)phenanthrene

Reagents, catalysts & solvents 3

HCID 178418397HCID 178418397, compoundCatalystHCID 6228DimethylformamideSolventHCID 8471TriethylamineSolvent

Procedure

2-iodo-7-propyl-phenanthrene in dimethylformamide and triethylamine was reacted with 4-ethynyl-1,2-difluorobenzene in the presence of tetrakis(triphenylphosphine)palladium (0), and the product was purified by silica gel column chromatography (hexane) and then recrystallized from ethanol to yield 2-propyl-7-(3,4-difluorophenylethynyl)phenanthrene.

Workup

  1. customthe product was purified by silica gel column chromatography (hexane)
  2. customrecrystallized from ethanol

Sources & evidence

ORD record
ord-ac944e5887e14e1e8f8962fe1013c3f8
Source dataset
uspto-grants-2006_06
Patent number
US07067179B1

Reaction notes

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