Hydrogen Bromide → 3-(5-Chloro-3-fluoropyridin-2-yl)-2-methyl-3-oxopropionic acid

HRID 650492

Reaction equation

HRID 650492 reaction equation
C([O:5][C:6](=[O:19])[CH:7]([CH3:18])[C:8]([C:10]1[C:15]([F:16])=[CH:14][C:13]([Cl:17])=[CH:12][N:11]=1)=[O:9])(C)(C)C.Br>C(O)(=O)C>[Cl:17][C:13]1[CH:14]=[C:15]([F:16])[C:10]([C:8](=[O:9])[CH:7]([CH3:18])[C:6]([OH:19])=[O:5])=[N:11][CH:12]=1

Participants

4

Reactant 2

HCID 260Hydrogen BromideHCID 220135773-(5-Chloro-3-fluoropyridin-2-yl)-2-methyl-3-oxopropionic acid tert-butyl ester

Product 1

HCID 217121243-(5-Chloro-3-fluoropyridin-2-yl)-2-methyl-3-oxopropionic acidYield 77.5%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

25.5 g of 3- (5-chloro-3-fluoropyridin-2-yl)-2-methyl-3-oxopropionic acid tert-but yl ester (Example P34) are added dropwise to 30 ml of a 33% solution of hydrogen bromide (HBr) in glacial acetic acid to form a suspension. The mixture is subsequently stirred for 90 minutes and then introduced into 300 ml of ice-water. The resulting precipitate is filtered off, washed with water and dried. 15.9 g of the desired title compound are obtained in the form of a solid having a melting point of 101-102° C.

Workup

  1. customto form a suspension
  2. filtrationThe resulting precipitate is filtered off
  3. washwashed with water
  4. customdried

Sources & evidence

ORD record
ord-40bab1da71314c42b076628190bd6e68
Source dataset
uspto-grants-2001_08
Patent number
US06274536B1

Linked notes

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