Toluene → 2-(4-Propylphenyl)-1,7,8-trifluoronaphthalene

HRID 1350609Notes

Reaction equation

HRID 1350609 reaction equation
FC(F)(F)S(O[C:7]1[CH:16]=[CH:15][C:14]2[C:9](=[C:10]([F:18])[C:11]([F:17])=[CH:12][CH:13]=2)[C:8]=1[F:19])(=O)=O.[CH2:22]([C:25]1[CH:30]=[CH:29][C:28](OB(O)O)=[CH:27][CH:26]=1)[CH2:23][CH3:24].C(=O)([O-])[O-].[K+].[K+].C1(C)C=CC=CC=1>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.O.O1CCCC1>[CH2:22]([C:25]1[CH:30]=[CH:29][C:28]([C:7]2[CH:16]=[CH:15][C:14]3[C:9](=[C:10]([F:18])[C:11]([F:17])=[CH:12][CH:13]=3)[C:8]=2[F:19])=[CH:27][CH:26]=1)[CH2:23][CH3:24]

Participants

8

Reactant 4

HCID 1140TolueneHCID 11430Potassium CarbonateHCID 21869456(4-Propylphenoxy)boronic acidHCID 23077305HCID 23077305, compound

Product 1

HCID 230773182-(4-Propylphenyl)-1,7,8-trifluoronaphthalene

Reagents, catalysts & solvents 3

HCID 178418397HCID 178418397, compoundCatalystHCID 962WaterSolvent2×HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
90 °C

Procedure

1,7,8-Trifluoronaphthalene-2-yl trifluoromethanesulfonate (15 g), 4-propylphenylboric acid (11.2 g), potassium carbonate (18.8 g), tetrakis(triphenylphosphine)palladium(0) (1 g), toluene (50 ml), tetrahydrofuran (50 ml), and water (20 ml) were added in an autoclave and stirred for 4 hours at 90° C. under pressurized nitrogen (2 kg/cm2). The reaction solution was poured into water. The organic layer was removed, and the aqueous layer was extracted with toluene. The organic layers were combined, washed with 10% hydrochloric acid and brine, and concentrated. The residue was purified by column chromatography (silica gel, hexane), and 2-(4-propylphenyl)-1,7,8-trifluoronaphthalene was obtained.

Workup

  1. customThe organic layer was removed
  2. extractionthe aqueous layer was extracted with toluene
  3. washwashed with 10% hydrochloric acid and brine
  4. concentrationconcentrated
  5. customThe residue was purified by column chromatography (silica gel, hexane)

Sources & evidence

ORD record
ord-c476342f05744014af73287ac2a5be62
Source dataset
uspto-grants-2007_05
Patent number
US07214835B2

Reaction notes

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