Iodine chloride → 2-Iodo-4-methyl-5-(trifluoromethyl)aniline
Reaction equation
[I:1]Cl.[CH3:3][C:4]1[CH:10]=[CH:9][C:7]([NH2:8])=[CH:6][C:5]=1[C:11]([F:14])([F:13])[F:12].C(=O)(O)[O-].[Na+]>ClCCl.CO.S(S([O-])=O)([O-])(=O)=O.[Na+].[Na+]>[I:1][C:9]1[CH:10]=[C:4]([CH3:3])[C:5]([C:11]([F:12])([F:13])[F:14])=[CH:6][C:7]=1[NH2:8]Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 3
Procedure
Add a solution of iodine monochloride (27.8 g, 171 mmol) in dichloromethane (180 mL) to a solution of 4-methyl-3-trifluoromethylaniline (25.0 g, 143 mmol) and sodium bicarbonate (14.4 g, 171 mmol) in methanol (180 mL) and dichloromethane (730 mL) at room temperature under nitrogen. Stir the mixture for 3 h and dilute the cooled mixture with aqueous sodium metabisulfite (500 mL). Collect the organic phase, and extract the aqueous phase with methylene chloride (200 mL). Wash the combined organic extracts with brine (250 mL), dry over anhydrous sodium sulfate and filter. Remove the solvent under reduced pressure to provide a brown oil, which crystallizes upon standing to afford the title compound as brown needles (44.4 g, >99%), which is used in the next step without purification. APCI MS m/z 302 (M+H)+.
Workup
- customCollect the organic phase
- extractionextract the aqueous phase with methylene chloride (200 mL)
- washWash the combined organic extracts with brine (250 mL)
- dry with materialdry over anhydrous sodium sulfate
- filtrationfilter
- customRemove the solvent under reduced pressure
- customto provide a brown oil, which
- customcrystallizes
Sources & evidence
- ORD record
- ord-6ef97865e4da4265acbc33d23ec58cbc
- Source dataset
- uspto-grants-2010_08
- Patent number
- US07786108B2
Reaction notes
Loading…