Reacción #556493

Ecuación de reacción

aluminium trichloride

thionyl chloride

DMF

2-bromopyridine-4-carboxylic acid

4-methyl-3H-benzoxazol-2-one

bromine

chlorine

→

6-(2-bromo-pyridine-4-carbonyl)-4-methyl-3H-benzoxazol-2-one

Disolventes

DCM

Condiciones de reacción

Tratamiento posterior

1. 1
   Temperaturarefluxed for 2 h
2. 2
   OtroThe reaction mixture was evaporated to dryness
3. 3
   Otrothe mixture obtained
4. 4
   Extracciónextracted twice with DCM
5. 5
   OtroThe organic phases were dried on magnesium sulphate
6. 6
   Filtraciónfiltered
7. 7
   Otroevaporated down i
8. 8
   OtroThe residue was triturated with DIPE/MeOH and suction
9. 9
   Filtraciónfiltered
10. 10
    OtroThe product obtained

Procedimiento

2.20 mL (30.0 mmol) thionyl chloride and 0.390 mL (4.80 mmol) DMF were added to 2.00 g (9.90 mmol) 2-bromopyridine-4-carboxylic acid in 30 mL DCM and refluxed for 2 h. The reaction mixture was evaporated to dryness and coevaporated twice with toluene. The residue was combined with 6.24 g (46.8 mmol) aluminium trichloride and 1.50 g (10.1 mmol) 4-methyl-3H-benzoxazol-2-one and the mixture obtained was stirred overnight at 110° C. and for 5 hours at 130° C. The mixture was decomposed with ice water and extracted twice with DCM. The organic phases were dried on magnesium sulphate, filtered and evaporated down i. vac. The residue was triturated with DIPE/MeOH and suction filtered. The product obtained is a mixture of the corresponding bromine and chlorine compound (40/60).

Fuente