4,4,5,5-Tetramethyl[1,3,2]dioxaborolane → Methyl 2-methyl-6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzoate

HRID 2105042Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2105042
I[C:2]1[CH:11]=[CH:10][CH:9]=[C:8]([CH3:12])[C:3]=1[C:4]([O:6][CH3:7])=[O:5].[CH3:13][C:14]1([CH3:21])[C:18]([CH3:20])([CH3:19])[O:17][BH:16][O:15]1>O1CCOCC1.CCOC(C)=O.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[CH3:12][C:8]1[CH:9]=[CH:10][CH:11]=[C:2]([B:16]2[O:17][C:18]([CH3:20])([CH3:19])[C:14]([CH3:21])([CH3:13])[O:15]2)[C:3]=1[C:4]([O:6][CH3:7])=[O:5]

Komponenten

6

Edukt 2

HCID 27347684,4,5,5-Tetramethyl[1,3,2]dioxaborolaneHCID 23655277Methyl 2-iodo-6-methylbenzoate

Produkt 1

HCID 68812827Methyl 2-methyl-6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzoateAusbeute 35 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 178418476HCID 178418476, VerbindungKatalysatorHCID 8857Ethyl AcetateLösungsmittelHCID 312751,4-DioxaneLösungsmittel

Reaktionsbedingungen

Temperatur
165 °C

Versuchsvorschrift

To a degassed mixture of methyl 2-iodo-6-methylbenzoate (220 mg, 0.9 mmol), 4,4,5,5-tetramethyl-1,3,2-dioxaborolane (0.16 mL, 1.1 mmol), TEA (0.4 mL, 2.7 mmol) in 2 mL dioxane was added Pd(PPh3)2Cl2 (20 mg, 0.03 mmol). The mixture was stirred at 165° C. for 10 min in a microwave oven. The mixture was diluted with EtOAc, washed with sat. NH4C1, H2O and brine, dried over (Na2SO4), filtered and concentrated. The crude product was purified by HPLC to afford 65 mg (35%) of Intermediate 296.1.

Aufarbeitung

  1. washwashed with sat. NH4C1, H2O and brine
  2. dry with materialdried over (Na2SO4)
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customThe crude product was purified by HPLC

Quellen und Nachweise

ORD-Eintrag
ord-3d07dc4c4e9b43b788d1ac8d51d814f7
Quelldatensatz
uspto-grants-2009_08
Patentnummer
US07576098B2

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