5-Chloro-2-methylbenzoxazole → Benzoxazole

HRID 520986

Reaktionsgleichung

Reaktionsgleichung von HRID 520986
Cl[C:2]1[CH:3]=[CH:4][C:5]2[O:9][C:8](C)=[N:7][C:6]=2[CH:11]=1.COC1C=CC=C(OC)C=1C1C=CC=CC=1P(C1CCCCC1)C1CCCCC1>CC([O-])=O.CC([O-])=O.[Pd+2]>[O:9]1[C:5]2[CH:4]=[CH:3][CH:2]=[CH:11][C:6]=2[N:7]=[CH:8]1

Komponenten

4

Edukt 2

HCID 295105-Chloro-2-methylbenzoxazoleHCID 112698722-Dicyclohexylphosphino-2',6'-dimethoxybiphenyl

Produkt 1

HCID 9228Benzoxazole

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 167845palladium(II) acetateKatalysator

Reaktionsbedingungen

Temperatur
100 °C

Versuchsvorschrift

To form 5-vinyl-2-methylbenzoxazole (4aa), the general procedure was followed using 5-chloro-2-methylbenzoxazole (3d) (167 mg, 1.01 mmol), vinyl MIDA boronate (2g) (218 mg, 1.19 mmol), SPhos (42 mg, 0.10 mmol) and Pd(OAc)2 (11 mg, 0.050 mmol). The reaction time and temperature were modified so that the reaction mixture was heated to 100° C. for 2 h. Benzoxazole 4aa was isolated as a pale golden liquid (152 mg, 96%). TLC (hexanes:EtOAc 3:1) Rf=0.46, visualized by UV (254 nm).

Quellen und Nachweise

ORD-Eintrag
ord-da86b1c1e8ba49c596ea65369b3e6128
Quelldatensatz
uspto-grants-2016_05
Patentnummer
US09328102B2

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