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5-Chloro-3-fluoro-2-phenylsulfinylpyridine → 5-Chloro-3-fluoro-2-(4-chloro-2-fluoro-5-methoxyphenyl)pyridine

HRID 2229124
Notes
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Reaction equation

HRID 2229124 reaction equation
[Cl:1][C:2]1[C:7]([O:8][CH3:9])=[CH:6][C:5]([Mg]Br)=[C:4]([F:12])[CH:3]=1.[Cl:13][C:14]1[CH:15]=[C:16]([F:28])[C:17](S(C2C=CC=CC=2)=O)=[N:18][CH:19]=1>C1COCC1>[Cl:13][C:14]1[CH:15]=[C:16]([F:28])[C:17]([C:5]2[CH:6]=[C:7]([O:8][CH3:9])[C:2]([Cl:1])=[CH:3][C:4]=2[F:12])=[N:18][CH:19]=1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

4

Reactant 2

HCID 184665225-Chloro-3-fluoro-2-phenylsulfinylpyridineHCID 178492975HCID 178492975, compound

Product 1

HCID 184665215-Chloro-3-fluoro-2-(4-chloro-2-fluoro-5-methoxyphenyl)pyridine

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
23 °C

Procedure

A Grignard solution of 12.9 g (0.049 mol) of 4-chloro-2-fluoro-5-methoxyphenylmagnesium bromide in 60 ml of THF was added with stirring at 23-30° C. to a solution of 10 g (0.0392 mol) of 5-chloro-3-fluoro-2-phenylsulfinylpyridine in 150 ml of THF over a period of 10 min, and the mixture was stirred at 23° C. for another 4 h. The reaction mixture was concentrated under reduced pressure, taken up in methylene chloride and extracted in succession with 1 N hydrochloric acid, 1 N of aqueous sodium hydroxide solution and with water, and dried. The solution was filtered with suction through silica gel, concentrated, stirred with pentane, filtered off with suction and dried, affording 5.7 g (50.1% of theory) of the title compound of mp. 120-122° C.

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. extractionextracted in succession with 1 N hydrochloric acid, 1 N of aqueous sodium hydroxide solution and with water
  3. customdried
  4. filtrationThe solution was filtered with suction through silica gel
  5. concentrationconcentrated
  6. stirringstirred with pentane
  7. filtrationfiltered off with suction
  8. customdried

Sources & evidence

ORD record
ord-057a878196874b5daa16b9318765e5a7
Source dataset
uspto-grants-2002_07
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US06420314B1

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes