Sulfuryl chloride → Ethyl 2-chloro-3-(2-chlorophenyl)-3-oxopropanoate

HRID 2282310Notes

Reaction equation

HRID 2282310 reaction equation
[CH2:1]([O:3][C:4](=[O:15])[CH2:5][C:6]([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=1[Cl:14])=[O:7])[CH3:2].S(Cl)([Cl:19])(=O)=O>CCOCC>[Cl:19][CH:5]([C:6]([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=1[Cl:14])=[O:7])[C:4]([O:3][CH2:1][CH3:2])=[O:15]

Participants

4

Reactant 2

HCID 24648Sulfuryl chlorideHCID 292405Ethyl (2-chlorobenzoyl)acetate

Product 1

HCID 13593390Ethyl 2-chloro-3-(2-chlorophenyl)-3-oxopropanoateYield 100%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

To a stirred solution of 3-(2-chloro-phenyl)-3-oxo-propionicacidethylester (5.000 mL, 26.600 mmol) in ether (75.00 mL) was added dropwise sulfuryl chloride (2.800 mL, 34.600 mmol) and the resulting solution was stirred for 4 h. The reaction mixture was diluted with ether (50.0 mL) and quenched by the slow addition of a saturated aqueous solution of sodium bicarbonate (50.0 mL) and the mixture was vigorously stirred for 30 min. The organic phase was separated and dried over anhydrous MgSO4, filtered, and concentrated in vacuo to provide 6.500 g of crude product as a clear colorless oil (100%). The crude residue was used without further purification. LC/MS (AA) ES+ 261, 263. 1H NMR (400 MHz, d, CDCl3) δ: 12.47 (s, 1H), 7.49-7.32 (m, 4H), 4.39 (q, J=7.2 Hz, 2H), 1.41 (t, J=7.2 Hz, 3H).

Workup

  1. customquenched by the slow addition of a saturated aqueous solution of sodium bicarbonate (50.0 mL)
  2. stirringthe mixture was vigorously stirred for 30 min
  3. customThe organic phase was separated
  4. dry with materialdried over anhydrous MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-da8f536096d649418a4aea2d271ed9e1
Source dataset
uspto-grants-2015_09
Patent number
US09139589B2

Reaction notes

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