Phosphorus oxychloride → 2-Chloro-5-iodo-3-(trifluoromethyl)pyridine
Reaction equation
[I:1][C:2]1[CH:3]=[C:4]([C:9]([F:12])([F:11])[F:10])[C:5](O)=[N:6][CH:7]=1.O=P(Cl)(Cl)[Cl:15]>CN(C=O)C>[Cl:15][C:5]1[C:4]([C:9]([F:12])([F:11])[F:10])=[CH:3][C:2]([I:1])=[CH:7][N:6]=1Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 110 °C
Procedure
A mixture of 5-iodo-3-(trifluoromethyl)pyridin-2-ol (53 g, 0.18 mmol) and POCl3 (67 mL, 0.73 mmol) in DMF (50 mL) was heated to 110° C. for 4 h. The reaction mixture was cooled to room temperature and then slowly poured into an ice/water bath. The brown solid was filtered and washed with water. It was then dissolved in DCM, washed with an aqueous saturated solution of sodium thiosulfate (2×), dried over sodium sulfate, and concentrated to dryness to afford 47 g of 2-chloro-5-iodo-3-(trifluoromethyl)pyridine as a pale yellow solid. 1H NMR (300 MHz, DMSO-d6) δ 8.79 (d, 1H), 8.29 (d, 1H).
Workup
- temperatureThe reaction mixture was cooled to room temperature
- additionslowly poured into an ice/water bath
- filtrationThe brown solid was filtered
- washwashed with water
- dissolutionIt was then dissolved in DCM
- washwashed with an aqueous saturated solution of sodium thiosulfate (2×)
- dry with materialdried over sodium sulfate
- concentrationconcentrated to dryness
Sources & evidence
- ORD record
- ord-003c7c54e2d94535aa59fc77155aa289
- Source dataset
- uspto-grants-2015_08
- Patent number
- US09108944B2
Reaction notes
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