Diisopropylamine → [2-Chloro-3-(trifluoromethyl)phenyl]methyl isocyanide
Reaction equation
[Cl:1][C:2]1[C:7]([C:8]([F:11])([F:10])[F:9])=[CH:6][CH:5]=[CH:4][C:3]=1[CH2:12][NH:13][CH:14]=O.C(NC(C)C)(C)C.P(Cl)(Cl)(Cl)=O.C(=O)([O-])O.[Na+]>ClCCl>[Cl:1][C:2]1[C:7]([C:8]([F:10])([F:11])[F:9])=[CH:6][CH:5]=[CH:4][C:3]=1[CH2:12][N+:13]#[C-:14]Participants
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 3.5 °C
Procedure
A solution of {[2-chloro-3-(trifluoromethyl)phenyl]methyl}formamide (0.67 g, 2.82 mmol) in anhydrous dichloromethane (20 ml) was cooled under argon in an ice-water bath before the addition of diisopropylamine (1.78 ml, 12.7 mmol) followed by phosphorus oxychloride (0.393 ml, 4.23 mmol). The reaction was stirred at between 2-5° C. for 2 hrs. The mixture was then reduced in vacuo and the residue treated with saturated aqueous sodium hydrogen carbonate (20 ml) and extracted with dichloromethane (20 ml). The organic layer was passed through a hydrophobic frit and the reduced in vacuo to give a yellow solid. Further drying in vacuo gave [2-chloro-3-(trifluoromethyl)phenyl]methyl isocyanide as an orange gum (0.66 g) which was used without further purification.
Workup
- extractionextracted with dichloromethane (20 ml)
- customto give a yellow solid
- customFurther drying in vacuo
Sources & evidence
- ORD record
- ord-8a7f7324880e447caf60995de0fbbff2
- Source dataset
- uspto-grants-2011_11
- Patent number
- US08048907B2
Reaction notes
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