Phenethyl bromide → HCID 18997129, compound

HRID 374459Notes

Reaction equation

HRID 374459 reaction equation
[N:1]1[CH:6]=[CH:5][C:4]([CH2:7][OH:8])=[CH:3][CH:2]=1.[Br:9][CH2:10][CH2:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1>CN(C)C=O>[Br-:9].[C:12]1([CH2:11][CH2:10][N+:1]2[CH:6]=[CH:5][C:4]([CH2:7][OH:8])=[CH:3][CH:2]=2)[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1

Participants

4

Reactant 2

HCID 7666Phenethyl bromideHCID 114724-Hydroxymethylpyridine

Product 1

HCID 18997129HCID 18997129, compoundYield 80%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 10.9 g of 4-pyridinemethanol, 25 g of 2-bromoethylbenzene an 30 mL of dimethylformamide was stirred in a 90° oil bath for 3 hours. Removal of the solvent and crystallization of the residue from 30 mL of ethanol gave 23.4 g (80%) of 1-(2-phenylethyl)-4-hydroxymethylpyridinium bromide, mp 132°-134°. NMR (DMSO) δ8.9 (d, 2H): 8.0 (d, 2H); 7.2-7.4 (m, 5H); 6.0 (t, 1H), 4.8-4.9 (d+t, 4H); 3.3 (t, 2H).

Workup

  1. customRemoval of the solvent and crystallization of the residue from 30 mL of ethanol

Sources & evidence

ORD record
ord-bb8fff86ce7c42619e4519e6a7bb6baf
Source dataset
uspto-grants-1996_01
Patent number
US05480892

Reaction notes

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