p-Chlorobenzenesulfonic acid → p-Toluenesulfonic acid monohydrate

HRID 227914

Reaktionsgleichung

Reaktionsgleichung von HRID 227914
Cl[C:2]1[CH:7]=[CH:6][C:5]([S:8]([OH:11])(=[O:10])=[O:9])=[CH:4][CH:3]=1.[CH3:12]B(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>[OH2:9].[C:2]1([CH3:12])[CH:7]=[CH:6][C:5]([S:8]([OH:11])(=[O:10])=[O:9])=[CH:4][CH:3]=1

Komponenten

7

Edukt 3

HCID 7400p-Chlorobenzenesulfonic acidHCID 11430Potassium CarbonateHCID 139377Methylboronic Acid

Produkt 1

HCID 521998p-Toluenesulfonic acid monohydrateAusbeute 217,6 %

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 4-chlorobenzenesulfonic acid (192 mg, 1.00 mmol), methylboronic acid (90 mg, 1.50 mmol), Pd(OAc)2 (2.2 mg, 0.010 mmol, 1 mol %), sodium 2-dicyclohexylphosphino-2′,6′-dimethoxybiphenyl-3′-sulfonate (10.0 mg, 0.020 mmol, 2 mol %), K2CO3 (414 mg, 3.00 mmol), water (2.0 mL), 12 h, 100° C. The product was isolated as a white solid (207 mg, 99%). Mp=104° C. (lit.=106° C.). 1H NMR (400 MHz, d4-MeOH) δ: 7.71 (d, 2H, J=8.4 Hz), 7.24 (d, 2H, J=8.4 Hz), 5.08 (s, H2O), 2.37 (s, 3H)). 13C NMR (125 MHz, d4-MeOH) δ: 143.3, 142.0, 130.0, 127.1, 21.4.

Quellen und Nachweise

ORD-Eintrag
ord-0bf4d5c14d6f46f88cb67dcd1ee045b4
Quelldatensatz
uspto-grants-2009_07
Patentnummer
US07560596B2

Verknüpfte Notizen

Wird geladen…