Ammonium Chloride → 3-(4-Bromo-2-methyl-phenyl)-3-cyano-propionic acid methyl ester
Reaction equation
C([N-]C(C)C)(C)C.[Li+].[Br:9][C:10]1[CH:15]=[CH:14][C:13]([CH2:16][C:17]#[N:18])=[C:12]([CH3:19])[CH:11]=1.Br[CH2:21][C:22]([O:24][CH3:25])=[O:23].[NH4+].[Cl-]>C1COCC1.O>[CH3:25][O:24][C:22](=[O:23])[CH2:21][CH:16]([C:13]1[CH:14]=[CH:15][C:10]([Br:9])=[CH:11][C:12]=1[CH3:19])[C:17]#[N:18]Participants
Reactant 4
Product 1
Reagents, catalysts & solvents 2
Procedure
Lithium diisopropylamide (2 M in THF, 110 mL) was added dropwise at −78° C. to a solution of (4-bromo-2-methyl-phenyl)-acetonitrile (38.55 g, 0.1835 mol) in THF (400 mL). The reaction mixture was stirred for 10 minutes and methyl bromoacetate (16.87 mL, 0.1835 mol) was added. The resulting mixture was stirred at −78° C. for 2 hours. A saturated solution of NH4Cl was then added at −78° C. and the resulting mixture was warmed to room temperature. Water was added and the mixture was extracted with EtOAc. The combined organic extracts were washed with water and brine; dried over MgSO4, filtered, and evaporated under reduced pressure. The residue was purified via flash chromatography (hexane/EtOAc, 9/1) to give 43.09 g of 3-(4-bromo-2-methyl-phenyl)-3-cyano-propionic acid methyl ester (83% yield) as a yellow oil.
Workup
- stirringThe resulting mixture was stirred at −78° C. for 2 hours
- extractionthe mixture was extracted with EtOAc
- washThe combined organic extracts were washed with water and brine
- dry with materialdried over MgSO4
- filtrationfiltered
- customevaporated under reduced pressure
- customThe residue was purified via flash chromatography (hexane/EtOAc, 9/1)
Sources & evidence
- ORD record
- ord-28c08f19384c47e49eed3747fdb5069b
- Source dataset
- uspto-grants-2010_08
- Patent number
- US07776910B2
Reaction notes
Loading…