N-bromobutanimide → Acetic acid 3-acetoxy-2-(4-amino-3-bromo-phenyl)-propyl ester

HRID 1190104Notes

Reaction equation

HRID 1190104 reaction equation
[C:1]([O:4][CH2:5][CH:6]([C:12]1[CH:17]=[CH:16][C:15]([NH2:18])=[CH:14][CH:13]=1)[CH2:7][O:8][C:9](=[O:11])[CH3:10])(=[O:3])[CH3:2].C1C(=O)N([Br:26])C(=O)C1>C(Cl)Cl>[C:9]([O:8][CH2:7][CH:6]([C:12]1[CH:17]=[CH:16][C:15]([NH2:18])=[C:14]([Br:26])[CH:13]=1)[CH2:5][O:4][C:1](=[O:3])[CH3:2])(=[O:11])[CH3:10]

Participants

4

Reactant 2

HCID 67184N-bromobutanimideHCID 15668325Acetic acid 3-acetoxy-2-(4-amino-phenyl)-propyl ester

Product 1

HCID 67187511Acetic acid 3-acetoxy-2-(4-amino-3-bromo-phenyl)-propyl esterYield 89%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of acetic acid 3-acetoxy-2-(4-amino-phenyl)-propyl ester (Tetrahedron, 46(20), 7081, (1990), 1.2 g, 5.0 mmol) in DCM (50 mL), NBS (903 mg, 5.07 mol) was added at 0° C. The resulting mixture was stirred at RT for 2 h and subjected to the usual work up to obtain acetic acid 3-acetoxy-2-(4-amino-3-bromo-phenyl)-propyl ester (1.4 g, 89%) which was directly used in the next step.

Sources & evidence

ORD record
ord-c6bf3ecaaf0e4804ae21bb61a4888d87
Source dataset
uspto-grants-2014_03
Patent number
US08674100B2

Reaction notes

Loading…