Triethylamine → 3-Methoxy-5-(trifluoromethyl)benzyl cyanide, 3-(Cyanomethyl)-5-methoxybenzotrifluoride
Reaction equation
C([N:3]([CH2:6][CH3:7])CC)C.[CH3:8][O:9][C:10]1[CH:11]=[C:12](CO)[CH:13]=[C:14]([C:16]([F:19])([F:18])[F:17])[CH:15]=1.CS(Cl)(=O)=O.[C-]#N.[Na+]>C(Cl)Cl.O.CN(C=O)C>[CH3:8][O:9][C:10]1[CH:11]=[C:12]([CH2:7][C:6]#[N:3])[CH:13]=[C:14]([C:16]([F:17])([F:18])[F:19])[CH:15]=1Participants
8
Reactant 4
Product 1
Reagents, catalysts & solvents 3
Conditions
- Temperature
- 0 °C
Procedure
Triethylamine (2.04 ml) was added to a solution of the product of step (ii) (3.02 g) in DCM (30 ml) and cooled to 0° C. before adding methane sulfonyl chloride (1.13 ml). The reaction mixture was stirred for 2 h at RT. The reaction mixture was diluted with water, extracted with DCM then dried (MgSO4) and evaporated under reduced pressure to give an oil. The oil was dissolved in DMF (20 ml), sodium cyanide (1.07 g) was added and stirred at 100° C. for 2 h. The reaction mixture was diluted with water, extracted with ether, dried (MgSO4) and evaporated under reduced pressure. The residue was purified by flash column chromatography (eluent ether) to give the subtitle compound (1.9 g).
Workup
- extractionextracted with DCM
- dry with materialthen dried (MgSO4)
- customevaporated under reduced pressure
- customto give an oil
- stirringstirred at 100° C. for 2 h
- extractionextracted with ether
- dry with materialdried (MgSO4)
- customevaporated under reduced pressure
- customThe residue was purified by flash column chromatography (eluent ether)
Sources & evidence
- ORD record
- ord-fbbb2337bef44960b88536f05a47fb41
- Source dataset
- uspto-grants-2012_04
- Patent number
- US08148572B2
Reaction notes
Loading…