1192474-21-7 → tert-Butyl (3-bromo-5-formylphenyl)carbamate
Reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([NH:10][C:11](=[O:17])[O:12][C:13]([CH3:16])([CH3:15])[CH3:14])[CH:5]=[C:6]([CH2:8][OH:9])[CH:7]=1>ClCCCl.[O-2].[Mn+4].[O-2]>[Br:1][C:2]1[CH:3]=[C:4]([NH:10][C:11](=[O:17])[O:12][C:13]([CH3:15])([CH3:14])[CH3:16])[CH:5]=[C:6]([CH:8]=[O:9])[CH:7]=1Participants
4
Reactant 1
Product 1
Reagents, catalysts & solvents 2
Conditions
- Temperature
- 80 °C
Procedure
A solution of tert-butyl [3-bromo-5-(hydroxymethyl)phenyl]carbamate (13.3 g, 44.2 mmol) and manganese(IV) oxide (19.2 g, 221 mmol) in 1,2-dichloroethane (88 mL) was stirred at 80° C. for 3 h. The reaction mixture was treated with additional manganese(IV) oxide (11.5 g, 132 mmol) and stirred at 80° C. for 16 h. The reaction mixture was filtered over celite (2×) and washed with dichloromethane. The filtrate was concentrated to give the desired product (10.9 g, 82% for 2 steps) as a white solid. LCMS for C12H14BrNO3Na (M+Na)+: m/z=321.9, 323.9.