Methyl iodide → 4-chloro-2-methyl-5-(methylsulfonyl)Benzoic acid

HRID 1368752Notes

Reaction equation

[Cl:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([OH:8])=[O:7])=[C:4]([CH3:11])[CH:3]=1.Cl[S:13]([OH:16])(=O)=[O:14].S([O-])([O-])=O.[Na+].[Na+].[CH3:23]I>>[CH3:11][C:4]1[CH:3]=[C:2]([Cl:1])[C:10]([S:13]([CH3:23])(=[O:16])=[O:14])=[CH:9][C:5]=1[C:6]([OH:8])=[O:7]

Participants

Reactant 4

HCID 6328Methyl iodide

HCID 24437Sodium Sulfite

HCID 24638Chlorosulfonic acid

HCID 3482694-Chloro-2-methylbenzoic acid

Product 1

HCID 108244784-chloro-2-methyl-5-(methylsulfonyl)Benzoic acid

Procedure

Accordingly, the invention also provides a process for the preparation of N-diaminomethylene-2-methyl-4,5-di(methylsulfonyl)benzamine, characterized in that in the first stage a) according to the invention 2-bromo-5-chlorotoluene is reacted with a secondary or tertiary organolithium compound, particularly preferably sec-butyllithium, and CO2 to give the first intermediate 4-chloro-2-methylbenzoic acid, in stage b) a methylsulfonyl group is introduced by reacting 4-chloro-2-methylbenzoic acid with chlorosulfonic acid, sodium sulfite and methyl iodide to give the corresponding intermediate 2-methyl-4-chloro-5-methylsulfonylbenzoic acid,

Workup

additionin stage b) a methylsulfonyl group is introduced

Sources & evidence

ORD record: ord-2e39b67b286844e49de78c100a7b1867
Source dataset: uspto-grants-2003_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06573404B2

Reaction notes

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