3-Phenoxybenzyl chloride → 3-Phenoxybenzyl fluoride

HRID 894335Notes

Reaction equation

HRID 894335 reaction equation
[O:1]([C:8]1[CH:9]=[C:10]([CH:13]=[CH:14][CH:15]=1)[CH2:11]Cl)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[F-:16].[K+]>[Br-].C([P+](CCCC)(CCCC)CCCCCCCCCCCCCCCC)CCC.O>[O:1]([C:8]1[CH:9]=[C:10]([CH:13]=[CH:14][CH:15]=1)[CH2:11][F:16])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 2

HCID 932913-Phenoxybenzyl chlorideHCID 522689Potassium Fluoride

Product 1

HCID 131945823-Phenoxybenzyl fluorideYield 49%

Reagents, catalysts & solvents 2

HCID 84716Hexadecyltributylphosphonium bromideCatalystHCID 962WaterSolvent

Conditions

Temperature
130 °C

Procedure

3-Phenoxybenzyl chloride (4.37 g), potassium fluoride (5.8 g), tri-n-butylhexadecylphosphonium bromide (1.2 g) and water (10 ml) were stirred for a period of 8 hours in a pressure bottle heated at a temperature of 130° C. The oil was separated and the aqueous phase was diluted with water and extracted with ethylene dichloride. The oil and ethylene dichloride extract were combined and the phosphonium salt was removed by chromatography over silica gel (15 g). The eluate was concentrated and distilled to give 3-phenoxybenzyl fluoride (1.96 g; 49%) b.p. 92°-95° C. at 0.3 mm Hg.

Workup

  1. customThe oil was separated
  2. additionthe aqueous phase was diluted with water
  3. extractionextracted with ethylene dichloride
  4. extractionThe oil and ethylene dichloride extract
  5. customthe phosphonium salt was removed by chromatography over silica gel (15 g)
  6. concentrationThe eluate was concentrated
  7. distillationdistilled

Sources & evidence

ORD record
ord-4fed7734b2c24a7a9f04a7951d25ccfb
Source dataset
uspto-grants-1981_08
Patent number
US04283414

Reaction notes

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