Hydrochloric Acid → HCID 66999437, compound
Reaction equation
[CH2:1]([O:3][C:4](=[O:24])[CH2:5][C:6]1[CH:11]=[CH:10][C:9](N)=[C:8]([O:13][C:14]2[CH:19]=[C:18]([C:20]#[N:21])[CH:17]=[C:16]([Br:22])[CH:15]=2)[C:7]=1[F:23])[CH3:2].C(ON=O)(C)(C)C.[ClH:32]>CC#N>[CH2:1]([O:3][C:4](=[O:24])[CH2:5][C:6]1[CH:11]=[CH:10][C:9]([Cl:32])=[C:8]([O:13][C:14]2[CH:19]=[C:18]([C:20]#[N:21])[CH:17]=[C:16]([Br:22])[CH:15]=2)[C:7]=1[F:23])[CH3:2]Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 60 °C
Procedure
The aniline 117b (3.98 g, 10.10 mmol) was dissolved in anhydrous CH3CN (35 mL) under nitrogen. This solution was then added dropwise to a mixture of tert-butylnitrite (2.40 mL, 20.20 mmol) and CuCl2 (2.72 g, 20.20 mmol) that had been prepared under nitrogen and warmed to 60° C. The reaction temperature was maintained at 60° C. for 2 h, then cooled to 0° C. A 5% aqueous HCl solution (80 mL) was added, and the mixture was extracted with 1:1 EtOAc/hexanes (3×75 mL). The combined organics were washed with brine (75 mL), dried over anhydrous MgSO4, and evaporated. The remaining oil was purified by flash chromatography on silica gel (0% to 30% EtOAc/Hexanes) to provide 2.67 g (64%) of the [4-chloro-3-(3-bromo-5-cyano-phenoxy)-2-fluoro-phenyl]-acetic acid ethyl ester (117c).
Workup
- customhad been prepared under nitrogen
- temperatureThe reaction temperature was maintained at 60° C. for 2 h
- temperaturecooled to 0° C
- extractionthe mixture was extracted with 1:1 EtOAc/hexanes (3×75 mL)
- washThe combined organics were washed with brine (75 mL)
- dry with materialdried over anhydrous MgSO4
- customevaporated
- customThe remaining oil was purified by flash chromatography on silica gel (0% to 30% EtOAc/Hexanes)
Sources & evidence
- ORD record
- ord-3f644c26e0344d7ea5a58e4c81f6145b
- Source dataset
- uspto-grants-2007_03
- Patent number
- US07189718B2
Reaction notes
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