1-Bromo-3-chloropropane → HCID 53719052, compound

HRID 1464150Notes

Reaction equation

HRID 1464150 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:11]([C:17]#[N:18])[C:12]([O:14][CH2:15][CH3:16])=[O:13])[CH:6]=[CH:7][C:8]=1[O:9][CH3:10].CC([O-])(C)C.[K+].Br[CH2:26][CH2:27][CH2:28][Cl:29]>CN(C)C=O>[Cl:29][CH2:28][CH2:27][CH2:26][C:4]1[C:3]([O:2][CH3:1])=[C:8]([O:9][CH3:10])[CH:7]=[CH:6][C:5]=1[CH:11]([C:17]#[N:18])[C:12]([O:14][CH2:15][CH3:16])=[O:13]

Participants

5

Reactant 3

HCID 80061-Bromo-3-chloropropaneHCID 12814070Ethyl cyano(3,4-dimethoxyphenyl)acetateHCID 23665647Potassium tert-butoxide

Product 1

HCID 53719052HCID 53719052, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

124.5 g (0.5 mol) of ethyl 3,4-dimethoxyphenylcyanoacetate in 160 ml of abs. dimethylformamide were added at 15°-20° while stirring to a suspension of 84.5 g (0.753 mol) of potassium tert-butylate in 300 ml of abs. dimethylformamide. After one hour 83.5 ml of 1-bromo-3-chloropropane were slowly added dropwise, whereby the temperature amounted to 15°-20°. After 16 hours the reaction mixture was evaporated in a high vacuum. The residue was partitioned between ether and an aqueous saturated ammonium chloride solution. The combined organic extracts were dried and evaporated under reduced pressure. The oily residue was distilled in a high vacuum, whereby 145.7 g of ethyl [γ-chloropropyl-3,4-dimethoxyphenyl]cyanoacetate were obtained, b.p. 195°-201°/80 Pa.

Workup

  1. customamounted to 15°-20°
  2. customAfter 16 hours the reaction mixture was evaporated in a high vacuum
  3. customThe residue was partitioned between ether
  4. customThe combined organic extracts were dried
  5. customevaporated under reduced pressure
  6. distillationThe oily residue was distilled in a high vacuum

Sources & evidence

ORD record
ord-7fa6ed8faa0d43dcbf2f68cc1802b357
Source dataset
uspto-grants-1994_04
Patent number
US05302727

Reaction notes

Loading…