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

HRID 2229124Notes

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

Participants

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

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