Toluene → 1-Fluoro-2-trifluoromethoxy-6-[(4-propylphenyl)ethynyl]naphthalene

HRID 992194Notes

Reaction equation

HRID 992194 reaction equation
[CH2:1]([C:4]1[CH:9]=[CH:8][C:7]([C:10]#[CH:11])=[CH:6][CH:5]=1)[CH2:2][CH3:3].Br[C:13]1[CH:22]=[CH:21][C:20]2[C:15](=[CH:16][CH:17]=[C:18]([O:24][C:25]([F:28])([F:27])[F:26])[C:19]=2[F:23])[CH:14]=1.C1(C)C=CC=CC=1>CN(C)C=O.[Cu](I)I.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>[F:23][C:19]1[C:20]2[C:15](=[CH:14][C:13]([C:11]#[C:10][C:7]3[CH:8]=[CH:9][C:4]([CH2:1][CH2:2][CH3:3])=[CH:5][CH:6]=3)=[CH:22][CH:21]=2)[CH:16]=[CH:17][C:18]=1[O:24][C:25]([F:28])([F:27])[F:26]

Participants

7

Reactant 3

HCID 1140TolueneHCID 27751331-Ethynyl-4-propylbenzeneHCID 218701542-Bromo-5-fluoro-6-trifluoromethoxynaphthalene

Product 1

HCID 218697581-Fluoro-2-trifluoromethoxy-6-[(4-propylphenyl)ethynyl]naphthaleneYield 36.6%

Reagents, catalysts & solvents 3

HCID 83717Copper iodideCatalystHCID 178418397HCID 178418397, compoundCatalystHCID 6228DimethylformamideSolvent

Procedure

10 g of 4-propyl-1-ethynylbenzene and 19.5 g of 2-bromo-5-fluoro-6-trifluoromethoxynaphthalene were dissolved in 50 ml of N,N-dimethylformamide (DMF). To the solution wore then added 50 mg of copper iodide (I) and 100 mg of tetrakis(triphenylphosphine)palladium (0). The reaction mixture was then stirred at room temperature for 5 hours. To the reaction solution was then added toluene. Insoluble matters were removed by filtration. The residue was then washed with water and saturated brine. The solvent was then distilled off. The residue was purified through silica gel column chromatography (hexane/ethyl acetate 9/1), and then recrystallized from ethanol to obtain 8.6 g of 1-fluoro-2-trifluoromethoxy-6-[(4-propylphenyl)ethynyl]naphthalene.

Workup

  1. customInsoluble matters were removed by filtration
  2. washThe residue was then washed with water and saturated brine
  3. distillationThe solvent was then distilled off
  4. customThe residue was purified through silica gel column chromatography (hexane/ethyl acetate 9/1)
  5. customrecrystallized from ethanol

Sources & evidence

ORD record
ord-d1051ed337994ffba6ad130a04bb622a
Source dataset
uspto-grants-2002_10
Patent number
US06468607B1

Reaction notes

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