Cesium fluoride → Fluoromethyl phenyl sulfide

HRID 926942Notes

Reaction equation

HRID 926942 reaction equation
[F-:1].[Cs+].[C:3]1([S:9][CH2:10]Cl)[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1>C(#N)C>[C:3]1([S:9][CH2:10][F:1])[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1

Participants

4

Reactant 2

HCID 25953Cesium fluorideHCID 81623Chloromethyl phenyl sulphide

Product 1

HCID 5314298Fluoromethyl phenyl sulfideYield 58.5%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

Cesium fluoride (191.50 g, 2 eq) was added to a mixture of PEG400 (100 mL) and acetonitrile (600 mL). The mixture was stirred for a few minutes under an argon atmosphere and then acetonitrile (100 mL) was removed by distillation. Chloromethyl phenyl sulfide (100 g, 630.32 mmol) was added and the resulting mixture was stirred for 6 hours at a temperature between 80° C. and 85° C. The mixture was filtered and the filtrate was concentrated. The crude product was purified by distillation to give 52.46 g (58.5%) of the desired product as slightly yellow oil (bp: 43° C. at 40 Pa).

Workup

  1. customacetonitrile (100 mL) was removed by distillation
  2. stirringthe resulting mixture was stirred for 6 hours at a temperature between 80° C. and 85° C
  3. filtrationThe mixture was filtered
  4. concentrationthe filtrate was concentrated
  5. distillationThe crude product was purified by distillation

Sources & evidence

ORD record
ord-eb217358a7d0434ba15d9c67c3dc7de9
Source dataset
uspto-grants-2016_03
Patent number
US09290446B2

Reaction notes

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