Dimethylformamide → 4-(4-Chlorophenoxy)-2-propylbenzaldehyde

HRID 1172817

Reaktionsgleichung

Reaktionsgleichung von HRID 1172817
FC(F)(F)S(O[C:7]1[CH:12]=[CH:11][C:10]([O:13][C:14]2[CH:19]=[CH:18][C:17]([Cl:20])=[CH:16][CH:15]=2)=[CH:9][C:8]=1[CH2:21][CH2:22][CH3:23])(=O)=O.C([SiH](CCCCCCCC)CCCCCCCC)CCCCCCC.C(N(CC)CC)C.C1(PC2C=CC=CC=2)C=CC=CC=1.CN([CH:74]=[O:75])C>C(OCC)(=O)C.O.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[Cl:20][C:17]1[CH:18]=[CH:19][C:14]([O:13][C:10]2[CH:11]=[CH:12][C:7]([CH:74]=[O:75])=[C:8]([CH2:21][CH2:22][CH3:23])[CH:9]=2)=[CH:15][CH:16]=1

Komponenten

9

Edukt 5

HCID 6228DimethylformamideHCID 8471TriethylamineHCID 70017DiphenylphosphineHCID 87780Trioctylsilane, 95%HCID 574201394-(4-Chlorophenoxy)-2-propylphenyl trifluoromethanesulfonate

Produkt 1

HCID 574201434-(4-Chlorophenoxy)-2-propylbenzaldehyde

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 167845palladium(II) acetateKatalysatorHCID 962WaterLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Reaktionsbedingungen

Temperatur
80 °C

Versuchsvorschrift

A mixture of the triflate from Step 6 of Example 1 (3.98 g, 10 mmol), trioctylsilane (6.7 mL, 15 mmol), triethyl amine (7.0 mL, 25 mmol), palladium acetate (0.22 g, 0.5 mmol) and diphenylphosphine (0.21 g, 0.5 mmol) in DMF (60 mL) was stirred at 80° C. under an atmosphere of carbon monoxide (50 psi) for 5 h. The reaction was then diluted with ethyl acetate and water. The organic layer was washed with water and concentrated. The residue was purified by chromatography on silica gel to give the title product.

Aufarbeitung

  1. washThe organic layer was washed with water
  2. concentrationconcentrated
  3. customThe residue was purified by chromatography on silica gel

Quellen und Nachweise

ORD-Eintrag
ord-3b6927da955b4e40becf93811e4e50c6
Quelldatensatz
uspto-grants-2010_11
Patentnummer
US07834036B2

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