Sodium ethoxide → 4-(4-Pentylbenzyloxy)-2,3-difluorobenzonitrile

HRID 1650605Notes

Reaction equation

HRID 1650605 reaction equation
[CH2:1]([C:6]1[CH:13]=[CH:12][C:9]([CH2:10]Cl)=[CH:8][CH:7]=1)[CH2:2][CH2:3][CH2:4][CH3:5].[F:14][C:15]1[C:20]([F:21])=[C:19]([C:22]#[N:23])[CH:18]=[CH:17][C:16]=1[OH:24].[O-]CC.[Na+]>C(O)C>[CH2:1]([C:6]1[CH:13]=[CH:12][C:9]([CH2:10][O:24][C:16]2[CH:17]=[CH:18][C:19]([C:22]#[N:23])=[C:20]([F:21])[C:15]=2[F:14])=[CH:8][CH:7]=1)[CH2:2][CH2:3][CH2:4][CH3:5]

Participants

5

Reactant 3

HCID 2723922Sodium ethoxideHCID 27369782,3-Difluoro-4-hydroxybenzonitrileHCID 122531741-(Chloromethyl)-4-pentylbenzene

Product 1

HCID 230519694-(4-Pentylbenzyloxy)-2,3-difluorobenzonitrile

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

A mixture of 0.12 mole of p-pentylbenzyl chloride and 20 ml of ethanol is added to a mixture of 0.1 mole of 2,3-difluoro-4-cyanophenol (prepared as in Example 1) and 0.1 mole of sodium ethoxide in 60 ml of ethanol, and the mixture is heated at the boil for 5 hours. After the ethanol has been distilled off, the reaction mixture is allowed to cool and is poured onto 15 ml of 5% aqueous sodium hydroxide solution. Working up in the customary manner gives 4-(4-pentylbenzyloxy)-2,3-difluorobenzonitrile.

Workup

  1. temperaturethe mixture is heated at the boil for 5 hours
  2. distillationAfter the ethanol has been distilled off
  3. temperatureto cool
  4. additionis poured onto 15 ml of 5% aqueous sodium hydroxide solution

Sources & evidence

ORD record
ord-66b0597f00fb48289ac7b23ae1f9b8d2
Source dataset
uspto-grants-1990_05
Patent number
US04925590

Reaction notes

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