Ethyl Acetate → 4-Bromo-2-ethoxy-5-methyl-1-[3-(trifluoromethyl)phenyl]-1H-imidazole
Reaction equation
C1C(=O)N([Br:8])C(=O)C1.[CH2:9]([O:11][C:12]1[N:13]([C:18]2[CH:23]=[CH:22][CH:21]=[C:20]([C:24]([F:27])([F:26])[F:25])[CH:19]=2)[C:14]([CH3:17])=[CH:15][N:16]=1)[CH3:10].C(OCC)(=O)C>CC#N.O.C(=O)([O-])[O-].[Na+].[Na+]>[Br:8][C:15]1[N:16]=[C:12]([O:11][CH2:9][CH3:10])[N:13]([C:18]2[CH:23]=[CH:22][CH:21]=[C:20]([C:24]([F:26])([F:27])[F:25])[CH:19]=2)[C:14]=1[CH3:17]Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 3
Procedure
A solution of NBS (5.16 g, 29 mmol) in MeCN (60 mL) was added to a stirred solution of 2-ethoxy-5-methyl-1-[3-(trifluoromethyl)phenyl]-1H-imidazole (7.92 g, 29 mmol) in MeCN (115 mL) at such a rate that the internal temperature of the mixture did not exceed 25° C. (a RT cooling bath was used). After 0.5 h the mixture was diluted with water (50 mL) and saturated sodium carbonate (aq) (50 mL). Ethyl acetate (50 mL) was added. The mixture was stirred vigorously then the phases were separated. The organic phase was washed with saturated brine (50 mL), dried (sodium sulfate) and concentrated in vacuo. The residue was taken into dichloromethane and filtered through a 25 g Si II SPE cartridge. The cartridge was washed with DCM and 10% EtOAc in DCM.
Workup
- customdid not exceed 25° C.
- customa RT
- temperaturecooling bath
- customthe phases were separated
- washThe organic phase was washed with saturated brine (50 mL)
- dry with materialdried (sodium sulfate)
- concentrationconcentrated in vacuo
- filtrationfiltered through a 25 g Si II SPE cartridge
- washThe cartridge was washed with DCM and 10% EtOAc in DCM
Sources & evidence
- ORD record
- ord-796635d23b6b48c1b8e38629ab136a81
- Source dataset
- uspto-grants-2016_08
- Patent number
- US09409870B2
Reaction notes
Loading…