Sodium Chloride → 5-Bromo-3-methyl-2,3-dihydro-1h-inden-1-one
Reaction equation
[Cl-].[Na+].[Cl-].[Al+3].[Cl-].[Cl-].[Br:7][C:8]1[CH:13]=[CH:12][C:11]([C:14](=[O:19])[CH2:15][CH2:16][CH2:17]Cl)=[CH:10][CH:9]=1>Cl>[Br:7][C:8]1[CH:13]=[C:12]2[C:11](=[CH:10][CH:9]=1)[C:14](=[O:19])[CH2:15][CH:16]2[CH3:17]Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 180 °C
Procedure
To a mixture of sodium chloride (1.23 g, 21.0 mmol) and aluminum chloride (5.0 g, 38.2 mmol) at 130° C. was added 1-(4-bromophenyl)-4-chlorobutan-1-one (1.0 g, 3.82 mmol) and the resulting mixture was heated to 180° C. for 20 minutes. The mixture was allowed to cool to room temperature and poured to a cold 1N aqueous HCl solution (300 mL). The mixture was extracted several times with dichloromethane. The combined organic layers were separated, dried over magnesium sulfate, filtered and concentrated to give 5-bromo-3-methyl-indan-1-one (0.77 g, 89%). The title compound, 1-methyl-5-(3-methyl-1-oxo-2,3-dihydro-1H-inden-5-yl)-1H-pyrrole-2-carbonitrile as an orange solid (0.65 g, 76%), was prepared from 5-bromo-3-methyl-indan-1-one and 1-methyl-2-cyanopyrrole according to the same coupling procedure as described in example 1. MS (ES) m/z 251.2; Anal. Calcd for C16H14N2O: C, 76.78; H, 5.64; N, 11.19. Found: C, 76.49; H, 5.49; N, 11.10. HRMS: calcd for C16H14N2O+H+, 251.1179; found (ESI, [M+H]+), 251.1179.
Workup
- temperatureto cool to room temperature
- extractionThe mixture was extracted several times with dichloromethane
- customThe combined organic layers were separated
- dry with materialdried over magnesium sulfate
- filtrationfiltered
- concentrationconcentrated
Sources & evidence
- ORD record
- ord-8913332038ce4b08ad7183283e8262e3
- Source dataset
- uspto-grants-2008_01
- Patent number
- US07319152B2
Reaction notes
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