Phosphorus oxychloride → 887707-33-7
Reaction equation
[Cl:1][CH2:2][C:3]1[CH:4]=[C:5]([C:11]([F:14])([F:13])[F:12])[C:6](OC)=[N:7][CH:8]=1.O=P(Cl)(Cl)[Cl:17]>CN(C=O)C>[Cl:17][C:6]1[C:5]([C:11]([F:14])([F:13])[F:12])=[CH:4][C:3]([CH2:2][Cl:1])=[CH:8][N:7]=1Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 100 °C
Procedure
To a cold solution of 5-(chloromethyl)-2-methoxy-3-(trifluoromethyl)pyridine (0.3 g, 1.33 mmol) in DMF (0.6 mL) was added dropwise POCl3 (1.02 g, 6.65 mmol). The reaction was stirred for 1 h at 100° C. in a sealed tube. The reaction was cooled to room temperature, and poured onto ice water (10 mL). The reaction was extracted with DCM (thrice) and the combined organic layer was washed with water and brine, dried with MgSO4 and concentrated. The residue was purified by silica gel column chromatography to provide the title compound (0.20 g). LCMS m/z=230.1 [M+H]+. 1H NMR (400 MHz, CDCl3) δ ppm 4.62 (s, 2H), 8.06 (d, J=2.3 Hz, 1H), 8.57 (d, J=2.3 Hz, 1H).
Workup
- temperatureThe reaction was cooled to room temperature
- additionpoured onto ice water (10 mL)
- extractionThe reaction was extracted with DCM (thrice)
- washthe combined organic layer was washed with water and brine
- dry with materialdried with MgSO4
- concentrationconcentrated
- customThe residue was purified by silica gel column chromatography
Sources & evidence
- ORD record
- ord-ca0d270e459847a39fae36a7e888708b
- Source dataset
- uspto-grants-2013_11
- Patent number
- US08580841B2
Reaction notes
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