Potassium Carbonate → 1,1'-Biphenyl, 2,2',4,6-tetramethyl-

HRID 227905

Reaktionsgleichung

Reaktionsgleichung von HRID 227905
Br[C:2]1[C:7]([CH3:8])=[CH:6][C:5]([CH3:9])=[CH:4][C:3]=1[CH3:10].[CH3:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=1B(O)O.C([O-])([O-])=O.[K+].[K+]>CC([O-])=O.CC([O-])=O.[Pd+2].C1(P(C2CCCCC2)C2C=CC=CC=2C2C(OC)=CC=C(S([O-])(=O)=O)C=2OC)CCCCC1.[Na+].O>[CH3:10][C:3]1[CH:4]=[C:5]([CH3:9])[CH:6]=[C:7]([CH3:8])[C:2]=1[C:13]1[CH:14]=[CH:15][CH:16]=[CH:17][C:12]=1[CH3:11]

Komponenten

7

Edukt 3

HCID 11430Potassium CarbonateHCID 684732-BromomesityleneHCID 27332672-Methylphenyl boronic acid

Produkt 1

HCID 116800841,1'-Biphenyl, 2,2',4,6-tetramethyl-Ausbeute 94 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 167845palladium(II) acetateKatalysatorHCID 23677046Sodium 2'-(dicyclohexylphosphino)-2,6-dimethoxybiphenyl-3-sulfonateKatalysatorHCID 962WaterLösungsmittel

Versuchsvorschrift

The general procedure described in Example 3 was used with 2-bromo-mesitylene (0.153 mL, 1.00 mmol), 2-methylphenylboronic acid (203 mg, 1.50 mmol), Pd(OAc)2 (4.5 mg, 0.020 mmol, 2 mol %), sodium 2-dicyclohexylphosphino-2′,6′-dimethoxybiphenyl-3′-sulfonate (20.0 mg, 0.040 mmol, 4 mol %), K2CO3 (276 mg, 2.00 mmol), water (1.5 mL), 22 h, room temperature. The product was isolated as a colorless oil (197 mg, 94%). 1H NMR (400 MHz, CDCl3) δ: 7.30-7.19 (m, 3H), 7.05-7.00 (m, 1H), 6.92 (s, 2H), 2.30 (2, 3H), 1.99 (s, 3H), 1.89 (s, 6H). 13C NMR (125 MHz, CDCl3) δ: 140.9, 138.2, 136.4, 136.0, 135.9, 130.0, 129.2, 128.1, 127.1, 126.2, 21.4, 20.6, 19.9.

Quellen und Nachweise

ORD-Eintrag
ord-b38e163c2ea04f769aac440c1ccc187f
Quelldatensatz
uspto-grants-2009_07
Patentnummer
US07560596B2

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