Sodium Chloride → 5-Azidomethyl-3-(4-bromo-phenyl)-4,5-dihydro-isoxazole

Participants

Role	Name	HCID	Charge
Reactant	Sodium Chloride	HCID 5234	—
Reactant	Sodium Azide	HCID 33557	—
Reactant	[3-(4-Bromophenyl)-4,5-dihydroisoxazol-5-yl]methyl methanesulfonate	HCID 18698757	—
Solvent	Dimethylformamide	HCID 6228	—
Product	5-Azidomethyl-3-(4-bromo-phenyl)-4,5-dihydro-isoxazole	HCID 17954468	112.7%

Reaction Conditions

Temperature	75 °C

Reaction Steps

Methanesulfonic acid 3-(4-bromo-phenyl)-4,5-dihydro-isoxazol-5-ylmethyl ester (55 g, 164.2 mmol) was added to dimethyl formamide (200 ml) followed by addition of sodium azide (21.4 g, 328.4 mmol). The mixture was heated to 75° C. for six hours and then added to aqueous sodium chloride (300 ml) followed by extraction with gethyl acetate (3×300 ml). The organic layers were combined, dried over sodium sulfate, and concentrated in vacuo to yield the desired product (52 g).

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US07396847B2
Source dataset	uspto-grants-2008_07
ORD ID	ord-e8cab888258b4224a137730ce68e6483
Source note	uspto-grants-2008_07