Iodine → 2-iodine-4 -(trifluoromethyl) anisole
Reaction equation
[CH3:1][O:2][C:3]1[CH:9]=[CH:8][C:7]([C:10]([F:13])([F:12])[F:11])=[CH:6][C:4]=1N.N(OC(C)(C)C)=O.[I:21]I>C(Cl)Cl>[I:21][C:4]1[CH:6]=[C:7]([C:10]([F:13])([F:12])[F:11])[CH:8]=[CH:9][C:3]=1[O:2][CH3:1]Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 70 °C
Procedure
To a stirred solution of 2-methoxy-5-(trifluoromethyl)aniline (500 mg, 2.62 mmol) in CH2Cl2 (10 mL) was added t-butyl nitrite (467 μL, 3.93 mmol). The reaction was stirred for 5 min prior to addition of iodine (1.3 g, 5.24 mmol), and then heated at 70° C. for 2 h. The reaction was cooled, diluted with CH2Cl2 (10 mL), washed with sat. Na2S2O3 (10 mL) and brine (10 mL), dried over Na2SO4, filtered and concentrated in vacuo. The crude product was purified by flash silica gel chromatography (hexanes) to afford 2-iodo-1-methoxy-4-(trifluoromethyl)benzene as a light yellow solid. 1H NMR (CDCl3, 500 MHz): δ 8.05 (d, J=2 Hz, 1 H), 7.61 (dd, J=8.7, 1.8 Hz, 1 H), 6.89 (d, J=8.7 Hz, 1 H), 3.97 (s, 3 H).
Workup
- temperatureThe reaction was cooled
- washwashed with sat. Na2S2O3 (10 mL) and brine (10 mL)
- dry with materialdried over Na2SO4
- filtrationfiltered
- concentrationconcentrated in vacuo
- customThe crude product was purified by flash silica gel chromatography (hexanes)
Sources & evidence
- ORD record
- ord-c46a75d80afd45b0b757b068b936273c
- Source dataset
- uspto-grants-2014_05
- Patent number
- US08735435B2
Reaction notes
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