tert-Butanol → (RS)-4-(5-bromo-2-fluoro-phenyl)-4-methyl-oxazolidin-2-one
Reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([F:8])=[C:4]([C:9]([N:13]=[C:14]=[O:15])([CH3:12])[CH2:10]I)[CH:3]=1.C([OH:20])(C)(C)C>CN(C)C=O.F[B-](F)(F)F.[Ag+]>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([F:8])=[C:4]([C:9]2([CH3:12])[CH2:10][O:20][C:14](=[O:15])[NH:13]2)[CH:3]=1Participants
5
Reactant 2
Product 1
Reagents, catalysts & solvents 2
Conditions
- Temperature
- 80 °C
Procedure
A solution of the crude (RS)-4-bromo-1-fluoro-2-(2-iodo-1-isocyanato-1-methyl-ethyl)-benzene (20.0 g, 52 mmol) in N,N-dimethylformamide (180 ml) and tert-butanol (7.7 ml, 104 mmol) was treated with silver tetrafluoroborate (11.15 g, 57 mmol). The yellow suspension was heated at 80° C. for 16 hours. For the workup, the reaction mixture was evaporated at reduced pressure. After chromatography on silica gel using a using a gradient of heptane and ethyl acetate=100/0 to 40/60 as the eluent, the (RS)-4-(5-bromo-2-fluoro-phenyl) -4-methyl-oxazolidin-2-one (intermediate C4A) was obtained as a white solid (28.49 g, 53.5% of theory).
Workup
- customFor the workup, the reaction mixture was evaporated at reduced pressure
Sources & evidence
- ORD record
- ord-a995bef918234afb8992ffc61741fd29
- Source dataset
- uspto-grants-2014_03
- Patent number
- US08673894B2
Reaction notes
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