3-Phenoxybenzyl chloride → HCID 13194582, compound

HRID 354698Notes

Reaction equation

HRID 354698 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 13194582HCID 13194582, compoundYield 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. (The product was stabilized by the addition of a small amount of anhydrous calcium carbonate to prevent acid catalysed polymerization).

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-cdcd3a4ab5264453a0fe4d4efc250155
Source dataset
uspto-grants-1983_03
Patent number
US04376784

Reaction notes

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