Potassium Carbonate → 2,4-Dichloro-3-ethenylbenzenamine
Reaction equation
[Cl:1][C:2]1[C:8](I)=[C:7]([Cl:10])[CH:6]=[CH:5][C:3]=1[NH2:4].C([O-])([O-])=O.[K+].[K+].CO[CH2:19][CH2:20]OC.O>[Pd].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>[Cl:1][C:2]1[C:8]([CH:19]=[CH2:20])=[C:7]([Cl:10])[CH:6]=[CH:5][C:3]=1[NH2:4]Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 80 °C
Procedure
To a solution of 2,4-dichloro-3-iodoaniline (9.0 g, 31 mmol) in DME/water (180 mLU60 mL) is added vinyl triboroxine pyridine complex (5.0 g, 20.8 mmol) and K2CO3 (8.5 g, 62.0 mmol). The reaction mixture is stirred and N2 is bubbled in for 15 min. Tetrakis(triphenylphosphine) palladium(0) (1.8 g, 1.6 mmol) is added at room temperature and N2 is bubbled in for additional 20 min. The reaction mixture is heated to 80° C. and stirred for 18 hours, when the GC-MS showed the reaction is complete. The mixture is filtered and washed with ether (400 mL) and water (50 mL). The organic layer is separated and washed with brine and dried over MgSO4. The solvents were removed and the residue is purified through a flash chromatographic column with a gradient of hexanes/ether to give 2,4-dichloro-3-vinylaniline.
Workup
- customN2 is bubbled in for 15 min
- customN2 is bubbled in for additional 20 min
- stirringstirred for 18 hours
- filtrationThe mixture is filtered
- washwashed with ether (400 mL) and water (50 mL)
- customThe organic layer is separated
- washwashed with brine
- dry with materialdried over MgSO4
- customThe solvents were removed
- customthe residue is purified through a flash chromatographic column with a gradient of hexanes/ether
Sources & evidence
- ORD record
- ord-1cdc9deae7d8401aaab6b04daaf6b352
- Source dataset
- uspto-grants-2013_01
- Patent number
- US08362294B2
Reaction notes
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