Diiodomethane → 2-Iodo-5-(trifluoromethyl)benzonitrile
Reaction equation
N[C:2]1[CH:9]=[CH:8][C:7]([C:10]([F:13])([F:12])[F:11])=[CH:6][C:3]=1[C:4]#[N:5].[I:14]CI.N(OC(C)(C)C)=O>C(#N)C.CCOCC>[I:14][C:2]1[CH:9]=[CH:8][C:7]([C:10]([F:13])([F:12])[F:11])=[CH:6][C:3]=1[C:4]#[N:5]Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 2
Conditions
- Temperature
- 35 °C
Procedure
To a solution of 2-amino-5-(trifluoromethyl)benzonitrile (Intermediate 7, 15.1 g) and diiodomethane (24 mL) in acetonitrile (150 mL) at 35° C. was added t-butyl nitrite (21 mL) dropwise. The reaction was maintained at approximately 35° C. during the addition. The reaction was aged for 30 min and then heated to 60° C. for 30 minutes. The reaction mixture was cooled, diluted with ether and washed twice with water, twice with aqueous sodium bisulfite, water and then brine. The solution was dried over anhydrous MgSO4, filtered through a silica gel plug and then concentrated giving afford a red oil. The product was purified by silica gel chromatography eluting sequentially with hexanes, 3:1 hexanes/CH2Cl2 and 1:1 hexanes/CH2Cl2 to afford 2-iodo-5-(trifluoromethyl)benzonitrile. 1H NMR (CDCl3, 500 MHz) δ 8.10 (d, J=8.5 Hz, 1H), 7.85 (d, J=1.8 Hz, 1H), 7.52 (dd, J=8.5, 1.8 Hz, 1H).
Workup
- temperatureheated to 60° C. for 30 minutes
- temperatureThe reaction mixture was cooled
- washwashed twice with water, twice with aqueous sodium bisulfite, water
- dry with materialThe solution was dried over anhydrous MgSO4
- filtrationfiltered through a silica gel plug
- concentrationconcentrated
- customgiving
- customafford a red oil
- customThe product was purified by silica gel chromatography
- washeluting sequentially with hexanes, 3:1 hexanes/CH2Cl2 and 1:1 hexanes/CH2Cl2
Sources & evidence
- ORD record
- ord-777f74b253174f98a126053b77adf9c9
- Source dataset
- uspto-grants-2011_03
- Patent number
- US07915271B2
Reaction notes
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