3-Chloro-2-(phenylsulfonyl)-5-(trifluoromethyl)pyridine → 2-(4-Chloro-2-fluoro-5-methoxyphenyl)-3-chloro-5-trifluoromethylpyridine

HRID 2187089Notes

Reaction equation

HRID 2187089 reaction equation
[Cl:1][C:2]1[C:3](S(C2C=CC=CC=2)(=O)=O)=[N:4][CH:5]=[C:6]([C:8]([F:11])([F:10])[F:9])[CH:7]=1.[Cl:21][C:22]1[C:27]([O:28][CH3:29])=[CH:26][C:25]([Mg]Br)=[C:24]([F:32])[CH:23]=1>C1COCC1>[Cl:21][C:22]1[C:27]([O:28][CH3:29])=[CH:26][C:25]([C:3]2[C:2]([Cl:1])=[CH:7][C:6]([C:8]([F:9])([F:10])[F:11])=[CH:5][N:4]=2)=[C:24]([F:32])[CH:23]=1

Participants

4

Reactant 2

HCID 14792663-Chloro-2-(phenylsulfonyl)-5-(trifluoromethyl)pyridineHCID 178492975HCID 178492975, compound

Product 1

HCID 110022952-(4-Chloro-2-fluoro-5-methoxyphenyl)-3-chloro-5-trifluoromethylpyridineYield 84%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

3-Chloro-2-phenylsulfonyl-5-trifluoromethylpyridine was stirred with 4-chloro-2-fluoro-5-methoxyphenylmagnesium bromide for 2.5 hours at room temperature in THF. Working-up by distillation gave the coupling product 2-(4-chloro-2-fluoro-5-methoxyphenyl)-3-chloro-5-trifluoromethylpyridine in a yield of 84%, which is outstanding.

Workup

  1. distillationWorking-up by distillation

Sources & evidence

ORD record
ord-1db5714982bc480a8c3fc46735997310
Source dataset
uspto-grants-2002_06
Patent number
US06407245B2

Reaction notes

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