Carbon tetrabromide → Ethyl 5-(bromomethyl)-1,2-oxazole-3-carboxylate

Carbon tetrabromide (5.44 g; 16.39 mmol) was added to the solution of triphenylphosphine (4.34 g, 16.39 mmol) in THF (50 mL) and the resulting mixture was stirred at room temperature for 15 min. To this green suspension was added a solution of ethyl 5-(hydroxymethyl)isoxazole-3-carboxylate (1.87 g, 10.93 mmol) in THF (10 mL) and the resulting reaction mixture was stirred overnight at room temperature. The solid material was removed by filtration. The filtrate was concentrated under reduced pressure and the residue was purified by flash chromatography on silica gel (eluent: 15 to 100% dichloromethane in heptane) to afford 1.73 g (68%) of ethyl 5-(bromomethyl)isoxazole-3-carboxylate as a solid.

1. customthe resulting reaction mixture
2. stirringwas stirred overnight at room temperature
3. customThe solid material was removed by filtration
4. concentrationThe filtrate was concentrated under reduced pressure
5. customthe residue was purified by flash chromatography on silica gel (eluent: 15 to 100% dichloromethane in heptane)

ORD record

ord-3bdb08645a304d71abee182697af6870

Source dataset

uspto-grants-2016_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09434722B2