Ethyl cyanoacetate → Ethyl 3-(4-bromophenyl)-2-cyanoprop-2-enoate

HRID 1617502Notes

Reaction equation

HRID 1617502 reaction equation
[Br:1][C:2]1[CH:9]=[CH:8][C:5]([CH:6]=O)=[CH:4][CH:3]=1.[C:10]([CH2:12][C:13]([O:15][CH2:16][CH3:17])=[O:14])#[N:11].N1CCCCC1>C1(C)C=CC=CC=1>[CH2:16]([O:15][C:13](=[O:14])[C:12]([C:10]#[N:11])=[CH:6][C:5]1[CH:8]=[CH:9][C:2]([Br:1])=[CH:3][CH:4]=1)[CH3:17]

Participants

5

Reactant 3

HCID 7764Ethyl cyanoacetateHCID 8082PiperidineHCID 707414-Bromobenzaldehyde

Product 1

HCID 367501Ethyl 3-(4-bromophenyl)-2-cyanoprop-2-enoateYield 90%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

To a solution of 4-bromo-benzaldehyde (5 g) and ethyl cyanoacetate (2.9 mL) in toluene (50 mL) was added piperidine (0.046 mL), and the mixture was stirred at reflux for 2 h with a Dean-Stark separator. The mixture was cooled to rt, stirred overnight and toluene was evaporated in vacuo. The crude residue was crystallized from EtOAc to yield the title compound (6.77 g, 90%) as a light yellow solid, MS (EI): m/z=279 ([M]+, 1Br).

Workup

  1. temperatureat reflux for 2 h with a Dean-Stark separator
  2. stirringstirred overnight
  3. customtoluene was evaporated in vacuo
  4. customThe crude residue was crystallized from EtOAc

Sources & evidence

ORD record
ord-27d9c19a64fc45d4872476ab5d8e54cc
Source dataset
uspto-grants-2014_07
Patent number
US08765730B2

Reaction notes

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