1-Bromooctane → 2-(4-Octyloxyphenyl)pyrimidine

HRID 1457489Notes

Reaction equation

HRID 1457489 reaction equation
[H-].[Na+].[OH:3][C:4]1[CH:9]=[CH:8][C:7]([C:10]2[N:15]=[CH:14][CH:13]=[CH:12][N:11]=2)=[CH:6][CH:5]=1.Br[CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH3:24]>CN(C)C=O>[CH2:17]([O:3][C:4]1[CH:5]=[CH:6][C:7]([C:10]2[N:11]=[CH:12][CH:13]=[CH:14][N:15]=2)=[CH:8][CH:9]=1)[CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH3:24]

Participants

5

Reactant 3

HCID 81401-BromooctaneHCID 24758Sodium hydrideHCID 1358026824-(2-Pyrimidinyl)phenol

Product 1

HCID 220990562-(4-Octyloxyphenyl)pyrimidineYield 65.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

0.30 g (7.50 mmol) of 60% strength sodium hydride are added in portions to 0.86 g (5.00 mmol) of 2-(4-hydroxyphenyl)pyrimidine in 40 ml of dimethylformamide, and the mixture is stirred at room temperature for 15 minutes. 1.45 g (7.50 mmol) of 1-bromooctane are subsequently added, the mixture is stirred overnight, poured into ice water and filtered, and the residue is purified by chromatography (silica gel/dichloromethane) and by recrystallization from acetonitrile, giving 0.93 g of 2-(4-octyloxyphenyl)pyrimidine. ##STR32##

Workup

  1. stirringthe mixture is stirred overnight
  2. filtrationfiltered
  3. customthe residue is purified by chromatography (silica gel/dichloromethane) and by recrystallization from acetonitrile

Sources & evidence

ORD record
ord-662156b41cf74ef9bdcb0d6a6ba90586
Source dataset
uspto-grants-1998_12
Patent number
US05849216

Reaction notes

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