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-b970f6b781674665951cc33ba500b657

Source dataset

uspto-grants-2013_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08618138B2