Potassium Phosphate, Tribasic → 2-Fluoro-4-chloro-6-cyclopropylaniline
Reaction equation
Br[C:2]1[C:7]([NH2:8])=[C:6]([F:9])[CH:5]=[C:4]([Cl:10])[CH:3]=1.[CH:11]1(B(O)O)[CH2:13][CH2:12]1.[O-]P([O-])([O-])=O.[K+].[K+].[K+].C1(P(C2CCCCC2)C2CCCCC2)CCCCC1>C1(C)C=CC=CC=1.O.CC([O-])=O.CC([O-])=O.[Pd+2]>[F:9][C:6]1[CH:5]=[C:4]([Cl:10])[CH:3]=[C:2]([CH:11]2[CH2:13][CH2:12]2)[C:7]=1[NH2:8]Participants
8
Reactant 4
Product 1
Reagents, catalysts & solvents 3
Conditions
- Temperature
- 90 °C
Procedure
6-Bromo-4-chloro-2-fluoroaniline (2.0 g, 8.91 mmol), cyclopropylboronic acid (1.53 g, 17.8 mmol), K3PO4 (6.61 g, 31.2 mmol) and tricyclohexyl phosphine (0.249 g, 0.89 mmol) are dissolved in toluene (31 mL) and water (10 mL). The solution is degassed with N2, heated to 90° C., and Pd(OAc)2 (0.25 g, 1.16 mmol) is added. The reaction mixture is heated at 100° C. for 18 hours, cooled over 48 hours and loaded directly on a column of silica gel for purification by column chromatography (EtOAc/hexanes) to give 2-fluoro-4-chloro-6-cyclopropylaniline.
Workup
- customThe solution is degassed with N2
- temperatureThe reaction mixture is heated at 100° C. for 18 hours
- temperaturecooled over 48 hours
- customloaded directly on a column of silica gel for purification by column chromatography (EtOAc/hexanes)
Sources & evidence
- ORD record
- ord-aff8222284864cd5ae20bcd05b5fc39d
- Source dataset
- uspto-grants-2007_04
- Patent number
- US07202364B2
Reaction notes
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