5-Chloro-2-methylbenzoxazole → Benzoxazole

HRID 520986

Reaction equation

HRID 520986 reaction equation
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

Participants

4

Reactant 2

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

Product 1

HCID 9228Benzoxazole

Reagents, catalysts & solvents 1

HCID 167845palladium(II) acetateCatalyst

Conditions

Temperature
100 °C

Procedure

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).

Sources & evidence

ORD record
ord-da86b1c1e8ba49c596ea65369b3e6128
Source dataset
uspto-grants-2016_05
Patent number
US09328102B2

Linked notes

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