Triethylamine → HCID 10063713, compound

HRID 963427Notes

Reaction equation

HRID 963427 reaction equation
[K+].[C:2]([O:8][CH2:9][CH3:10])(=[O:7])[CH2:3][C:4]([O-:6])=O.C(N(CC)CC)C.[Cl-].[Mg+2].[Cl-].[Br:21][C:22]1[CH:30]=[CH:29][C:25](C(Cl)=O)=[C:24]([Cl:31])[CH:23]=1>C(#N)C>[Br:21][C:22]1[CH:30]=[CH:29][C:25]([C:4](=[O:6])[CH2:3][C:2]([O:8][CH2:9][CH3:10])=[O:7])=[C:24]([Cl:31])[CH:23]=1

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 3446434Potassium ethyl malonateHCID 5360315Magnesium ChlorideHCID 155922074-Bromo-2-chlorobenzoyl chloride

Product 1

HCID 10063713HCID 10063713, compoundYield 86.4%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

13bs) 6.8 g of monoethyl malonate potassium salt in 70 ml of acetonitrile were cooled to 10° under argon and treated with 5.3 ml of triethylamine and 4.8 g of magnesium chloride. The resulting thick suspension was stirred at room temperature for 2 hrs. Then, it was again cooled to 10° and 5 g of 4-bromo-2-chloro-benzoyl chloride were added dropwise thereto over 30 min. The mixture was stirred at room temperature for 15 hrs. and then concentrated. Extraction: twice with 100 ml of toluene, once with 100 ml of cold 1N HCl and twice with 100 ml of water. After drying and evaporation there were obtained 5.2 g (85%) of ethyl 3-(4-bromo-2-chlorophenyl)-3-oxo-propionate as a brown oil which crystallized in a refrigerator. M.p. 34° C.

Workup

  1. temperatureThen, it was again cooled to 10°
  2. waitover 30 min
  3. stirringThe mixture was stirred at room temperature for 15 hrs
  4. concentrationand then concentrated
  5. extractionExtraction
  6. customAfter drying
  7. customevaporation there

Sources & evidence

ORD record
ord-7db676c7d7454471a21c9701eed604c3
Source dataset
uspto-grants-1998_06
Patent number
US05763450

Reaction notes

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