N-Methylaniline → HCID 86681320, compound
Reaction equation
Br[C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([Br:8])[C:3]=1[CH3:9].[CH3:10][NH:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1>C1(C)C=CC=CC=1>[Br:8][C:4]1[C:3]([CH3:9])=[C:2]([N:11]([CH3:10])[C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[CH:7]=[CH:6][CH:5]=1Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 85 °C
Procedure
1,3-Dibromo-2-methylbenzene (5.01 g) and N-methylaniline (1.00 g) were added to toluene (65 mL). The solution was degassed and flushed with nitrogen three times. Cesium carbonate (9.12 g), 2,2′-bis(diphenylphosphino)-1,1′-binaphthyl (0.872 g), and palladium (II) acetate (0.314 g) were added. The solution was degassed and flushed with nitrogen and then heated to 85° C. for 72 hours. The solution was cooled, added to 1 M aqueous HCl, and extracted with diethyl ether. The extract was washed with brine, dried on anhydrous sodium sulfate, filtered, and concentrated under vacuum. The crude material was purified on silica gel using 2% ethyl acetate in hexanes.
Workup
- customThe solution was degassed
- customflushed with nitrogen three times
- additionCesium carbonate (9.12 g), 2,2′-bis(diphenylphosphino)-1,1′-binaphthyl (0.872 g), and palladium (II) acetate (0.314 g) were added
- customThe solution was degassed
- customflushed with nitrogen
- temperatureThe solution was cooled
- additionadded to 1 M aqueous HCl
- extractionextracted with diethyl ether
- washThe extract was washed with brine
- dry with materialdried on anhydrous sodium sulfate
- filtrationfiltered
- concentrationconcentrated under vacuum
- customThe crude material was purified on silica gel using 2% ethyl acetate in hexanes
Sources & evidence
- ORD record
- ord-4955be46b3834d96b49661314222c4b2
- Source dataset
- uspto-grants-2015_01
- Patent number
- US08940737B2
Reaction notes
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