Water → HCID 21869386, compound

HRID 857606Notes

Reaction equation

HRID 857606 reaction equation
[CH2:1]([C:4]1[CH:9]=[CH:8][C:7](OB(O)O)=[CH:6][CH:5]=1)[CH2:2][CH3:3].FC(F)(F)S(O[C:20]1[CH:21]=[C:22]2[C:27](=[CH:28][CH:29]=1)[C:26]([F:30])=[C:25]([O:31][C:32]([F:35])([F:34])[F:33])[C:24]([F:36])=[CH:23]2)(=O)=O.O.C1(C)C=CC=CC=1>CN(C=O)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>[F:30][C:26]1[C:27]2[C:22](=[CH:21][C:20]([C:7]3[CH:8]=[CH:9][C:4]([CH2:1][CH2:2][CH3:3])=[CH:5][CH:6]=3)=[CH:29][CH:28]=2)[CH:23]=[C:24]([F:36])[C:25]=1[O:31][C:32]([F:35])([F:33])[F:34]

Participants

7

Reactant 4

HCID 962WaterHCID 1140TolueneHCID 21869456(4-Propylphenoxy)boronic acidHCID 542655381,3-Difluoro-2-trifluoromethoxynaphthalene-6-yl trifluoromethanesulfonate

Product 1

HCID 21869386HCID 21869386, compoundYield 61.9%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 6228DimethylformamideSolvent

Conditions

Temperature
85 °C

Procedure

7.3 g of 4-propylphenylboric acid and 11 g of 1,3-difluoro-2-trifluoromethoxynaphthalene-6-yl trifluoromethanesulfonate (obtained by triflating 1,3-difluoro-2-trifluoromethoxynaphthalene-6-ol with trifluoromethanesulfonic anhydride) were dissolved in 50 ml of DMF. To the solution was then added 0.4 g of tetrakis(triphenylphosphine)palladium (0). The reaction mixture was stirred at a temperature of 85° C. for 8 hours. To the reaction solution were then added water and toluene. The resulting aqueous phase was then extracted with toluene. The material thus extracted and the organic phase were together washed with water and then with saturated brine, and then dried over anhydrous sodium sulfate. The solvent was then distilled off under reduced pressure to obtain an oily matter. The oily matter thus obtained was purified through silica gel column chromatography (hexane/ethyl acetate=9/1), and then recrystallized from ethanol to obtain 6.3 g of 1,3-difluoro-2-trifluoromethoxy-6-(4-propylphenyl)naphthalene in crystal form.

Workup

  1. extractionThe resulting aqueous phase was then extracted with toluene
  2. extractionThe material thus extracted
  3. washthe organic phase were together washed with water
  4. dry with materialwith saturated brine, and then dried over anhydrous sodium sulfate
  5. distillationThe solvent was then distilled off under reduced pressure
  6. customto obtain an oily matter
  7. customThe oily matter thus obtained
  8. customwas purified through silica gel column chromatography (hexane/ethyl acetate=9/1)
  9. customrecrystallized from ethanol

Sources & evidence

ORD record
ord-f5e2dc8a695c4b818a99dc3fdbf456e9
Source dataset
uspto-grants-2006_12
Patent number
US07145047B2

Reaction notes

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