Phenethyl bromide → HCID 18997146, compound

HRID 374461Notes

Reaction equation

HRID 374461 reaction equation
[C:1]([O:9][CH2:10][CH3:11])(=[O:8])[C:2]1[CH:7]=[CH:6][N:5]=[CH:4][CH:3]=1.[Br:12][CH2:13][CH2:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1>CC(O)C>[Br-:12].[C:15]1([CH2:14][CH2:13][N+:5]2[CH:6]=[CH:7][C:2]([C:1]([O:9][CH2:10][CH3:11])=[O:8])=[CH:3][CH:4]=2)[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1

Participants

4

Reactant 2

HCID 7666Phenethyl bromideHCID 15291Ethyl isonicotinate

Product 1

HCID 18997146HCID 18997146, compoundYield 80.3%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

A mixture of 5.00 g (33 mmol) of ethyl isonicotinate, 6.12 g (33 mmol) of 2-bromoethylbenzene and 25 mL of 2-propanol were heated at reflux for 17 hours. The mixture was evaporated to dryness and triturated 3×75 mL with ether. The excess ether was removed by evaporation and there was obtained 8.91 g of 1-(2-phenylethyl)-4-carboethoxypyridinium bromide as a yellow solid. NMR (CDCl3) 58.97 (d, 2H); 8.34 (d, 2H); 7.13-7.2 6 (m, 5H); 5.35-5.42 (m, 2H); 4.41-4.50 (q, 2H); 3.39-3.47 (t, 2H); 2.58-2.65 (m, 2H); 1.37-1.46 (t, 3H).

Workup

  1. temperaturewere heated
  2. temperatureat reflux for 17 hours
  3. customThe mixture was evaporated to dryness
  4. customtriturated 3×75 mL with ether
  5. customThe excess ether was removed by evaporation

Sources & evidence

ORD record
ord-bda9381a38b54218afaa42b18969ee58
Source dataset
uspto-grants-1996_01
Patent number
US05480892

Reaction notes

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