Reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][C:5]([Cl:11])=[C:6]([CH:10]=1)C(O)=O.C1(P(N=[N+]=[N-])(C2C=CC=CC=2)=[O:19])C=CC=CC=1.CC[N:31]([CH2:34]C)CC.[C:36]([OH:40])([CH3:39])([CH3:38])[CH3:37]>>[C:36]([O:40][C:34](=[O:19])[NH:31][C:6]1[CH:10]=[C:2]([Br:1])[CH:3]=[CH:4][C:5]=1[Cl:11])([CH3:39])([CH3:38])[CH3:37]Participants
5
Procedure
A solution of 5-Bromo-2-Chloro benzoic acid (24 g, 0.1 mol), di-phenylphosphoryl azide (28 mL, 1.3 eq), and Et3N (140 mL, 10 eq) in tert-butanol (300 mL) was refluxed for 3 hrs. The resulting solution was concentrated under reduced pressure, diluted with ether (300 mL) and washed with HCl 1N (300 mL), saturated solution of NaHCO3 (200 mL), and brine (200 mL). The organic layers was dried over anhydrous sodium sulfate and concentrated. Chromatography on silica (EtOAc/n-hexane) yielded, (26 g, 85%).
Workup
- concentrationThe resulting solution was concentrated under reduced pressure
- additiondiluted with ether (300 mL)
- washwashed with HCl 1N (300 mL), saturated solution of NaHCO3 (200 mL), and brine (200 mL)
- dry with materialThe organic layers was dried over anhydrous sodium sulfate
- concentrationconcentrated
- customChromatography on silica (EtOAc/n-hexane) yielded
Sources & evidence
- ORD record
- ord-5f414bda7e1746bea9e738391638c0ce
- Source dataset
- uspto-grants-2011_10
- Patent number
- US08044041B2
Linked notes
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