Boron tribromide → HCID 135776387, compound

Participants

Reaction Conditions

Reaction Steps

Boron tribromide (102 ml of a 1 M solution in CH2Cl2) was added dropwise to a solution of thiadiazole 7 (8.0 g, 26.84 mmol) in CH2Cl2 (30 ml) at -78° C. After 2 hours the resulting dark green solution was warmed to 0° C. and quenched with 5% HCl. The aqueous layer was extracted twice with EtOAc. The organic layers were combined, dried over MgSO4, and the solvent was removed under reduced pressure. The crude yellow solid was dissolved in EtOAc and extracted twice with 5% NaOH. The aqueous layer was acidified with 10% HCl, and extracted twice with EtOAc. The organic layers were combined, dried over MgSO4, and the solvent was removed under reduced pressure. The resulting white solid was recrystallized from MeOH/H2O to afford 28 (5.58 g, 77.1%), m.p. 221.0°-222.0°60 C.

Provenance & Evidence