Sulfuric Acid → HCID 22664966, compound

HRID 277391Notes

Reaction equation

HRID 277391 reaction equation
[Cl:1][C:2]1[CH:10]=[CH:9][CH:8]=[CH:7][C:3]=1[C:4](Cl)=[O:5].Br[C:12]([CH3:19])([CH3:18])[C:13]([O:15][CH2:16][CH3:17])=[O:14].S(=O)(=O)(O)O>[Zn].CCOCC>[Cl:1][C:2]1[CH:10]=[CH:9][CH:8]=[CH:7][C:3]=1[C:4](=[O:5])[C:12]([CH3:19])([C:13]([O:15][CH2:16][CH3:17])=[O:14])[CH3:18]

Participants

6

Reactant 3

HCID 1118Sulfuric AcidHCID 11745Propanoic acid, 2-bromo-2-methyl-, ethyl esterHCID 691102-Chlorobenzoyl chloride

Product 1

HCID 22664966HCID 22664966, compoundYield 55.1%

Reagents, catalysts & solvents 2

HCID 23994ZincCatalystHCID 3283Diethyl EtherSolvent

Procedure

A mixture of 2-chlorobenzoyl chloride (52.2 g, 0.298 mol), ethyl 2-bromoisobutyrate (58.2 g, 0.298 mol) and ether is added in portions to zinc foil (19.5 g, 0.298 mol) and the resultant mixture stirred at reflux for three hours and overnight at room temperature. The mixture is poured into cold, dilute sulfuric acid and the organic layer is washed with saturated sodium bicarbonate and brine, dried over anhydrous magnesium sulfate and concentrated in vacuo to a yellow oil. The oil is chromatographed on silica gel with hexanes:ethyl acetate to afford the title compound as a colorless oil (41.8 g, 55.1%)

Workup

  1. washthe organic layer is washed with saturated sodium bicarbonate and brine
  2. dry with materialdried over anhydrous magnesium sulfate
  3. concentrationconcentrated in vacuo to a yellow oil
  4. customThe oil is chromatographed on silica gel with hexanes

Sources & evidence

ORD record
ord-8c12290add7f4fc4ada8aea82bef35e7
Source dataset
uspto-grants-2002_03
Patent number
US06355796B1

Reaction notes

Loading…