Ethyl cyanoacetate → HCID 21855808, compound

HRID 1448688Notes

Reaction equation

HRID 1448688 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([C:8]([F:11])([F:10])[F:9])=[CH:4][CH:3]=1.[Mg].[C:13]([CH2:15][C:16]([O:18][CH2:19][CH3:20])=[O:17])#[N:14]>CCOCC>[NH2:14][C:13]([C:2]1[CH:7]=[CH:6][C:5]([C:8]([F:11])([F:10])[F:9])=[CH:4][CH:3]=1)=[CH:15][C:16]([O:18][CH2:19][CH3:20])=[O:17]

Participants

5

Reactant 3

HCID 7764Ethyl cyanoacetateHCID 67872Benzene, 1-bromo-4-(trifluoromethyl)-HCID 5462224Magnesium

Product 1

HCID 21855808HCID 21855808, compoundYield 87.4%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

To the Grignard reagent prepared from 98 g (0.436 mol) of p-bromobenzotrifluoride and 10.59 g (0.436 mol) of magnesium in ether was added 24.65 g (0.218 mol) of ethyl cyanoacetate dropwise with stirring and cooling in an ice bath. The resultant mixture was stirred at reflux for 24 hours. The usual workup gave 49.4 g of dark red-brown residue; distillation of this material gave 16.73 g (30%) of product, boiling point 120°-123° (0.15 torr).

Workup

  1. temperaturecooling in an ice bath
  2. temperatureat reflux for 24 hours

Sources & evidence

ORD record
ord-2f15156646334df6a1d426f66563d566
Source dataset
uspto-grants-1980_02
Patent number
US04187099

Reaction notes

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