Potassium Carbonate → Methyl 2-[(acetyloxy)methyl]-2'-methylbiphenyl-4-carboxylate

HRID 1950840Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1950840
[C:1]([O:4][CH2:5][C:6]1[CH:7]=[C:8]([CH:13]=[CH:14][C:15]=1Br)[C:9]([O:11][CH3:12])=[O:10])(=[O:3])[CH3:2].[C:17]1([CH3:26])[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=1B(O)O.C(=O)([O-])[O-].[K+].[K+]>C1(C)C=CC=CC=1.O.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>[C:1]([O:4][CH2:5][C:6]1[CH:7]=[C:8]([C:9]([O:11][CH3:12])=[O:10])[CH:13]=[CH:14][C:15]=1[C:18]1[CH:19]=[CH:20][CH:21]=[CH:22][C:17]=1[CH3:26])(=[O:3])[CH3:2]

Komponenten

7

Edukt 3

HCID 11430Potassium CarbonateHCID 27332672-Methylphenyl boronic acidHCID 22574808Methyl 3-(acetoxymethyl)-4-bromobenzoate

Produkt 1

HCID 67400282Methyl 2-[(acetyloxy)methyl]-2'-methylbiphenyl-4-carboxylateAusbeute 100,1 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 178418397HCID 178418397, VerbindungKatalysatorHCID 962WaterLösungsmittelHCID 1140TolueneLösungsmittel

Versuchsvorschrift

A mixture of methyl 3-[(acetyloxy)methyl]-4-bromobenzoate (4.7 g; 16.4 mmol; 1 eq.), o-tolylboronic acid (2.45 g; 18 mmol; 1.1 eq.), potassium carbonate (11.3 g; 82 mmol; 5 eq.) and Pd(PPh3)4 (1.89 g; 1.64 mmol; 0.1 eq.) in toluene (23.5 mL) and water (23.5 mL) was refluxed for 2 hours. After cooling to room temperature, the reaction mixture was filtered through a pad of Celite® which was further washed with toluene (50 mL). The filtrate was concentrated in vacuo, the residue taken up in ethyl acetate (250 mL) and washed with sat. aq. NaHCO3 (100 mL), water (100 mL) and brine (100 mL), dried over magnesium sulphate and concentrated in vacuo to afford the title compound (4.9 g, 100%) as a brown oil.

Aufarbeitung

  1. temperaturewas refluxed for 2 hours
  2. filtrationthe reaction mixture was filtered through a pad of Celite® which
  3. washwas further washed with toluene (50 mL)
  4. concentrationThe filtrate was concentrated in vacuo
  5. washwashed with sat. aq. NaHCO3 (100 mL), water (100 mL) and brine (100 mL)
  6. dry with materialdried over magnesium sulphate
  7. concentrationconcentrated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-9e55212143884f749a438341d6b8e394
Quelldatensatz
uspto-grants-2013_03
Patentnummer
US08404676B2

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