Water → Ethyl 3-(2-bromo-6-chlorophenyl)propanoate

HRID 1471676Notes

Reaction equation

HRID 1471676 reaction equation
[Br:1][C:2]1[CH:19]=[CH:18][CH:17]=[C:16]([Cl:20])[C:3]=1[CH2:4][CH:5](C(OCC)=O)[C:6]([O:8][CH2:9][CH3:10])=[O:7].O.[Cl-].[Li+]>CS(C)=O>[Br:1][C:2]1[CH:19]=[CH:18][CH:17]=[C:16]([Cl:20])[C:3]=1[CH2:4][CH2:5][C:6]([O:8][CH2:9][CH3:10])=[O:7]

Participants

5

Reactant 3

HCID 962Water2×HCID 433294Lithium ChlorideHCID 67983387Diethyl 2-(2-bromo-6-chlorobenzyl)malonate

Product 1

HCID 67982372Ethyl 3-(2-bromo-6-chlorophenyl)propanoate

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

Diethyl 2-(2-bromo-6-chlorobenzyl)malonate (13.0 g, 35.7 mmol), water (1.29 mL, 71.5 mmol) and lithium chloride (3.03 g, 71.50 mmol) in dimethylsulfoxide (75 mL) were heated to +185° C. for 1 h. The solution was allowed to cool. 75 mL of water was added. The mixture was extracted with ethyl acetate. The organic phase was washed with water and aqueous NaHCO3. The organic phase was separated, dried over MgSO4, filtered and the solvent was removed by rotary evaporation to give the title compound. Yield: 7.34 g, 70%. 1H NMR (500 MHz, CDCl3) δ ppm 1.27-1.30 (m, 3H) 2.55-2.61 (m, 2H) 3.27-3.33 (m, 2H) 4.16-4.21 (m, 2H) 7.02 (t, 1H) 7.31-7.35 (m, 1H) 7.45-7.50 (m, 1H). MS m/z 293.0 [M+H]+.

Workup

  1. temperatureto cool
  2. extractionThe mixture was extracted with ethyl acetate
  3. washThe organic phase was washed with water and aqueous NaHCO3
  4. customThe organic phase was separated
  5. dry with materialdried over MgSO4
  6. filtrationfiltered
  7. customthe solvent was removed by rotary evaporation

Sources & evidence

ORD record
ord-bf30eeae73224437a1780998dc140f49
Source dataset
uspto-grants-2015_04
Patent number
US09012457B2

Reaction notes

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