Toluene → Methyl 1-(2-cyanophenyl)cyclopropanecarboxylate
Reaction equation
Br[CH2:2][CH2:3]Br.[OH-].[Na+].C1(C)C=CC=CC=1.[C:14]([C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=1[CH2:22][C:23]([O:25][CH3:26])=[O:24])#[N:15]>[Br-].C([N+](CCCC)(CCCC)CCCC)CCC.O>[C:14]([C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=1[C:22]1([C:23]([O:25][CH3:26])=[O:24])[CH2:3][CH2:2]1)#[N:15]Participants
Procedure
1.5 g of tetra-n-butylammonium bromide, 6.5 g of 1,2-dibromoethane and 20 mL of aqueous 50% sodium hydroxide solution were added to a toluene (40 mL) solution of 4.0 g of methyl 2-cyanophenylacetate, and stirred at room temperature for 1 hour. Water was added to the reaction liquid, and extracted with ethyl acetate. The organic layer was washed with saturated saline water, dried with anhydrous magnesium sulfate, and the solvent was evaporated away under reduced pressure. The crude product was purified through silica gel column chromatography (hexane/ethyl acetate) to obtain 3.0 g of the entitled compound as a colorless compound. 1H-NMR (400 MHz, CDCl3) δ: 7.66 (1H, dd, J=7.6, 1.2 Hz), 7.55 (1H, td, J=7.6, 1.2 Hz), 7.43-7.36 (2H, m), 3.66 (3H, s), 1.82 (2H, q, J=3.7 Hz), 1.30 (2H, q, J=3.7 Hz) ESI-MS Found: m/z [M+H] 202.
Workup
- extractionextracted with ethyl acetate
- washThe organic layer was washed with saturated saline water
- dry with materialdried with anhydrous magnesium sulfate
- customthe solvent was evaporated away under reduced pressure
- customThe crude product was purified through silica gel column chromatography (hexane/ethyl acetate)
Sources & evidence
- ORD record
- ord-a1101ced932b48f3987eeadbcb6c7fef
- Source dataset
- uspto-grants-2016_05
- Patent number
- US09345705B2
Reaction notes
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