Sodium Iodide → 2-Iodo-4-[3-(trifluoromethoxy)phenyl]pyridine

HRID 2207643Notes

Reaction equation

C(Cl)(=O)C.Cl[C:6]1[CH:11]=[C:10]([C:12]2[CH:17]=[CH:16][CH:15]=[C:14]([O:18][C:19]([F:22])([F:21])[F:20])[CH:13]=2)[CH:9]=[CH:8][N:7]=1.[I-:23].[Na+].C(=O)([O-])[O-].[Na+].[Na+].S(S([O-])=O)([O-])(=O)=O.[Na+].[Na+]>CC#N.CCOC(C)=O.O>[I:23][C:6]1[CH:11]=[C:10]([C:12]2[CH:17]=[CH:16][CH:15]=[C:14]([O:18][C:19]([F:22])([F:21])[F:20])[CH:13]=2)[CH:9]=[CH:8][N:7]=1

Participants

Conditions

Temperature: 80 °C

Procedure

Acetyl chloride (4.45 mL, 62.6 mmol) was added to a solution of 2-chloro-4-[3-(trifluoromethoxy)phenyl]-pyridine [CAS 1261856-64-7](11.42 g, 41.73 mmol) and sodium iodide (31.28 g, 208.67 mmol) in MeCN (200 mL) under N2, and the resulting suspension was heated at 80° C. for 18 hrs. Additional sodium iodide was added (20 mol %) and stirring was continued for 3 hrs. The reaction was cooled and the mixture was treated with aqueous sodium carbonate. After 5 minutes, solid sodium metabisulphite was added until decolourisation achieved. Water was added to redissolve a precipitate which had formed. The mixture was diluted with EtOAc and the layers separated. The aqueous layer was washed with EtOAc (2x), the combined organics were dried (MgSO4) and the solvent evaporated to afford the crude 2-iodo-4-[3-(trifluoromethoxy)phenyl]pyridine (D105) (16.3 g) as a amber oil containing about ˜5% of reduced 2-H material and ˜8% of unreacted chloride starting material;

Workup

temperatureThe reaction was cooled
waitAfter 5 minutes
dissolutionto redissolve a precipitate which
customhad formed
customthe layers separated
washThe aqueous layer was washed with EtOAc (2x)
dry with materialthe combined organics were dried (MgSO4)
customthe solvent evaporated

Sources & evidence

ORD record: ord-f2f47785b669408f9e61181f65129054
Source dataset: uspto-grants-2016_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09376436B2

Reaction notes

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