Boron tribromide → N-Trifluoroacetyl-8-bromo-7-hydroxy-1-isopropyl-2,3,4,5-tetrahydro-1H-3-benzazepine
Reaction equation
[F:1][C:2]([F:23])([F:22])[C:3]([N:5]1[CH2:11][CH:10]([CH:12]([CH3:14])[CH3:13])[C:9]2[CH:15]=[C:16]([Br:21])[C:17]([O:19]C)=[CH:18][C:8]=2[CH2:7][CH2:6]1)=[O:4].B(Br)(Br)Br>ClCCl>[F:23][C:2]([F:1])([F:22])[C:3]([N:5]1[CH2:11][CH:10]([CH:12]([CH3:14])[CH3:13])[C:9]2[CH:15]=[C:16]([Br:21])[C:17]([OH:19])=[CH:18][C:8]=2[CH2:7][CH2:6]1)=[O:4]Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 20 °C
Procedure
A solution of N-trifluoroacetyl-8-bromo-1-isopropyl-7-methoxy-2,3,4,5-tetrahydro-1H-3-benzazepine (0.041 g, 0.10 mmol) in dichloromethane (1 mL) was treated with BBr3 (0.32 ml, 1.0 M solution in CH2Cl2) and stirred overnight at 20° C. The excess BBr3 is quenched with water and the resulting mixture diluted with ether (50 mL), washed twice with saturated aqueous Na2CO3 (20 mL) and concentrated. Flash chromatography (20% EtOAc in hexanes, silica) resulted in 0.037 g clear oil. MS calculated for C15H17BrF3NO2+H: 380, observed: 380.
Workup
- customThe excess BBr3 is quenched with water
- additionthe resulting mixture diluted with ether (50 mL)
- washwashed twice with saturated aqueous Na2CO3 (20 mL)
- concentrationconcentrated
Sources & evidence
- ORD record
- ord-7b53f547dbe341c2ad7532c2dc0b88b9
- Source dataset
- uspto-grants-2013_10
- Patent number
- US08546378B2
Reaction notes
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