3-Fluorophenol → 2-Cyano-3-(3-fluorophenoxymethyl)pyridine

HRID 1741590Notes

Reaction equation

HRID 1741590 reaction equation
[O-]CC.[Na+].[Na].[F:6][C:7]1[CH:8]=[C:9]([OH:13])[CH:10]=[CH:11][CH:12]=1.Br[CH2:15][C:16]1[C:17]([C:22]#[N:23])=[N:18][CH:19]=[CH:20][CH:21]=1>C(O)C>[C:22]([C:17]1[C:16]([CH2:15][O:13][C:9]2[CH:10]=[CH:11][CH:12]=[C:7]([F:6])[CH:8]=2)=[CH:21][CH:20]=[CH:19][N:18]=1)#[N:23]

Participants

6

Reactant 4

HCID 97433-FluorophenolHCID 2723922Sodium ethoxideHCID 5360545SodiumHCID 103754503-(Bromomethyl)pyridine-2-carbonitrile

Product 1

HCID 102631622-Cyano-3-(3-fluorophenoxymethyl)pyridine

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a chilled solution of sodium ethoxide, prepared from 13.8 g of sodium metal and 240 ml of absolute ethanol, 56.9 ml of 3-fluorophenol was added and the mixture was stirred at room temperature for 30 minutes. Crude 3-bromomethyl-2-cyanopyridine (103 g) was added to the mixture at 5° C., and the mixture was reflexed for 2 hours. After being concentrated, the reaction mixture was diluted with ether, and the resultant insoluble materials were removed by filtration. The filtrate was washed with 10% aqueous sodium hydroxide solution and with water, dried over anhydrous sodium sulfate, and then concentrated. The residue was crystallized by trituration with a mixture of ether and n-hexane to yield 58.0 g of pale brown crystals, which were recrystallized from isopropyl ether to give pale yellow needles, mp 52°-53° C.

Workup

  1. additionwas added
  2. waitthe mixture was reflexed for 2 hours
  3. concentrationAfter being concentrated
  4. additionthe reaction mixture was diluted with ether
  5. customthe resultant insoluble materials were removed by filtration
  6. washThe filtrate was washed with 10% aqueous sodium hydroxide solution and with water
  7. dry with materialdried over anhydrous sodium sulfate
  8. concentrationconcentrated
  9. customThe residue was crystallized by trituration with a mixture of ether and n-hexane

Sources & evidence

ORD record
ord-32e8dcd982d54917ba69b9a170485f54
Source dataset
uspto-grants-1994_08
Patent number
US05334594

Reaction notes

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