Iodine → 6-Fluoro-3-iodo-4,5-dihydro-1H-benzo[b]azepin-2(3H)-one
Reaction equation
[F:1][C:2]1[C:7]2[CH2:8][CH2:9][CH2:10][C:11](=[O:13])[NH:12][C:6]=2[CH:5]=[CH:4][CH:3]=1.CN(CCN(C)C)C.[I:22][Si](C)(C)C.II>C(Cl)Cl>[F:1][C:2]1[C:7]2[CH2:8][CH2:9][CH:10]([I:22])[C:11](=[O:13])[NH:12][C:6]=2[CH:5]=[CH:4][CH:3]=1Participants
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 0 °C
Procedure
6-Fluoro-1,3,4,5-tetrahydro-1-benzazepin-2-one (25 g, 140 mmol) was charged to a 100-mL three neck flask with a dropping funnel and an overhead stirrer. DCM (250 ml) is added and the reaction is cooled to 0° C. TMEDA (29.5 ml, 195 mmol) is added, followed by drop wise addition of iodotrimethylsilane (26.6 ml, 195 mmol). The mixture was stirred for 45 minutes. Iodine (49.6 g, 195 mmol) is added in 5 portions and the mixture is stirred for another 1.5 h. The reaction was quenched with 250 mL Na2SO3 (aqueous solution). The solids were dissolved in dichloromethane and the layers separated. The organic layer is washed with water, dried over Na2SO4, and concentrated to give 6-fluoro-3-iodo-1,3,4,5-tetrahydro-1-benzazepin-2-one (42.5 g) as a brown solid.
Workup
- stirringthe mixture is stirred for another 1.5 h
- customThe reaction was quenched with 250 mL Na2SO3 (aqueous solution)
- dissolutionThe solids were dissolved in dichloromethane
- customthe layers separated
- washThe organic layer is washed with water
- dry with materialdried over Na2SO4
- concentrationconcentrated
Sources & evidence
- ORD record
- ord-636a1d17359d46919e917ed7300a3f76
- Source dataset
- uspto-grants-2013_11
- Patent number
- US08575150B2
Reaction notes
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