Dimethylformamide → 2-Bromo-6-chloro-4-(1-chloroethyl)-3-ethoxybenzonitrile
Reaction equation
N1C(Cl)=NC(Cl)=NC=1[Cl:3].CN(C)C=O.[Br:15][C:16]1[C:23]([O:24][CH2:25][CH3:26])=[C:22]([CH:27](O)[CH3:28])[CH:21]=[C:20]([Cl:30])[C:17]=1[C:18]#[N:19].C(Cl)Cl>>[Br:15][C:16]1[C:23]([O:24][CH2:25][CH3:26])=[C:22]([CH:27]([Cl:3])[CH3:28])[CH:21]=[C:20]([Cl:30])[C:17]=1[C:18]#[N:19]Participants
Procedure
Cyanuric chloride (0.11 g, 0.59 mmol) was dissolved in N,N-dimethylformamide (3 mL, 40 mmol). After stirring for a few minutes, a solution of 2-bromo-6-chloro-3-ethoxy-4-(1-hydroxyethyl)benzonitrile (150 mg, 0.49 mmol) in methylene chloride (3 mL, 50 mmol) was added. The resulting mixture was stirred at room temperature overnight. The reaction was partitioned between water and dichloromethane. The organic layer was washed with sat. NaHCO3 solution, water, brine, dried over MgSO4, and concentrated. The crude product was purified by flash column chromatography, eluting a gradient of 0-30% EtOAc/Hexane to give 2-bromo-6-chloro-4-(1-chloroethyl)-3-ethoxybenzonitrile (0.12 gm, 75%) as a semisolid, LCMS calculated for C11H10BrCl2NO m/z=323.9, 320.9; found: (poor ionization).
Workup
- stirringThe resulting mixture was stirred at room temperature overnight
- customThe reaction was partitioned between water and dichloromethane
- washThe organic layer was washed with sat. NaHCO3 solution, water, brine
- dry with materialdried over MgSO4
- concentrationconcentrated
- customThe crude product was purified by flash column chromatography
- washeluting a gradient of 0-30% EtOAc/Hexane
Sources & evidence
- ORD record
- ord-2cfc2100b04a4906aac43b8cb25f2f0b
- Source dataset
- uspto-grants-2015_12
- Patent number
- US09199982B2
Reaction notes
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