Water → HCID 59713008, compound
Reaction equation
[F:1][C:2]([F:11])([F:10])[C:3]1[CH:4]=[C:5](Br)[CH:6]=[CH:7][CH:8]=1.[Mg].Br[CH:14]([CH3:20])[C:15]([O:17][CH2:18][CH3:19])=[O:16].O>O1CCCC1.[Cl-].[Zn+2].[Cl-].CCOCC>[CH2:18]([O:17][C:15](=[O:16])[CH:14]([C:5]1[CH:6]=[CH:7][CH:8]=[C:3]([C:2]([F:11])([F:10])[F:1])[CH:4]=1)[CH3:20])[CH3:19]Participants
Conditions
- Temperature
- 55 °C
Procedure
3-Trifluoromethylbromobenzene 50 (0.2 mol) was dissolved in dry tetrahydrofuran (100 mL). A small amount of magnesium metal was added and the mixture was warmed until reaction commenced. Additional magnesium (0.2 mol) was added. The mixture was maintained at reflux until the magnesium was consumed. A solution of anhydrous zinc chloride (0.2 mol) in tetrahydrofuran (50 mL) was added. The mixture was maintained at 55° C. for 2 hours, and then ethyl 2-bromopropionate (0.2 mol) was added. The mixture was maintained at 55° C. and the progress of the reaction was monitored by TLC. When the reaction was complete, the mixture was cooled and added to water and ether. The organic layer was dried and concentrated, and the residue was chromatographed to afford 2-(3-trifluoromethyl-phenyl)-propionic acid ethyl ester 51.
Workup
- temperaturethe mixture was warmed until reaction commenced
- temperatureThe mixture was maintained
- customwas consumed
- temperatureThe mixture was maintained at 55° C.
- temperaturethe mixture was cooled
- customThe organic layer was dried
- concentrationconcentrated
- customthe residue was chromatographed
Sources & evidence
- ORD record
- ord-b43dc8300f2443ecac273fc81a02770a
- Source dataset
- uspto-grants-2008_05
- Patent number
- US07371888B2
Reaction notes
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