2-Bromo-1-(3-chloro-5-(trifluoromethyl)phenyl)ethanone → 2-(3-Chloro-5-(trifluoromethyl)phenyl)-2-oxoethyl methyl succinate

HRID 534843Notes

Reaction equation

HRID 534843 reaction equation
Br[CH2:2][C:3]([C:5]1[CH:10]=[C:9]([C:11]([F:14])([F:13])[F:12])[CH:8]=[C:7]([Cl:15])[CH:6]=1)=[O:4].[CH3:16][O:17][C:18](=[O:24])[CH2:19][CH2:20][C:21]([O-:23])=[O:22].[Na+]>CC(C)=O>[C:21]([O:23][CH2:2][C:3]([C:5]1[CH:10]=[C:9]([C:11]([F:14])([F:13])[F:12])[CH:8]=[C:7]([Cl:15])[CH:6]=1)=[O:4])(=[O:22])[CH2:20][CH2:19][C:18]([O:17][CH3:16])=[O:24]

Participants

4

Reactant 2

HCID 197023082-Bromo-1-(3-chloro-5-(trifluoromethyl)phenyl)ethanoneHCID 21362364Sodium 4-methoxy-4-oxobutanoate

Product 1

HCID 667508792-(3-Chloro-5-(trifluoromethyl)phenyl)-2-oxoethyl methyl succinateYield 91.3%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A stirred suspension of 2-bromo-1-(3-chloro-5-(trifluoromethyl)phenyl)ethanone (Reference Example 34, 1.05 g, 3.48 mmol) and sodium 4-methoxy-4-oxobutanoate (0.805 g, 5.22 mmol) in acetone (50.0 mL) was heated at reflux overnight. After that time the reaction mixture was cooled to room temperature and adsorbed onto silica gel (4.30 g). The residue was purified by flash column chromatography (silica gel, hexanes/ethyl acetate 4:1) to provide 2-(3-chloro-5-(trifluoromethyl)phenyl)-2-oxoethyl methyl succinate (1.12 g, 91%) as a pale yellow oil.

Workup

  1. temperaturewas heated
  2. temperatureat reflux overnight
  3. customThe residue was purified by flash column chromatography (silica gel, hexanes/ethyl acetate 4:1)

Sources & evidence

ORD record
ord-99e71064f878435da7af3e4bff4f5da9
Source dataset
uspto-grants-2014_10
Patent number
US08853215B2

Reaction notes

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