3,4-Difluorophenylacetylene → HCID 22045565, compound

HRID 1830481Notes

Reaction equation

HRID 1830481 reaction equation
I[C:2]1[CH:14]=[CH:13][C:12]2[C:11]3[C:6](=[CH:7][C:8]([CH2:15][CH2:16][CH3:17])=[CH:9][CH:10]=3)[CH2:5][C:4]=2[CH:3]=1.[C:18]([C:20]1[CH:25]=[CH:24][C:23]([F:26])=[C:22]([F:27])[CH:21]=1)#[CH:19]>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>[CH2:15]([C:8]1[CH:9]=[CH:10][C:11]2[C:12]3[C:4](=[CH:3][C:2]([C:19]#[C:18][C:20]4[CH:25]=[CH:24][C:23]([F:26])=[C:22]([F:27])[CH:21]=4)=[CH:14][CH:13]=3)[CH2:5][C:6]=2[CH:7]=1)[CH2:16][CH3:17]

Participants

6

Reactant 2

HCID 138784543,4-DifluorophenylacetyleneHCID 22045128HCID 22045128, compound

Product 1

HCID 22045565HCID 22045565, compound

Reagents, catalysts & solvents 3

HCID 178418397HCID 178418397, compoundCatalystHCID 6228DimethylformamideSolventHCID 8471TriethylamineSolvent

Procedure

2-iodo-7-propyl-fluorene 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)fluorene.

Workup

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

Sources & evidence

ORD record
ord-aac585daf9ac42e7980f88c7c92e567c
Source dataset
uspto-grants-2006_06
Patent number
US07067179B1

Reaction notes

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