Diethyl Ether → HCID 21262958, compound

HRID 357269Notes

Reaction equation

HRID 357269 reaction equation
[Mg].Br[C:3]1[CH:8]=[CH:7][C:6]([F:9])=[CH:5][CH:4]=1.[CH2:10]([S:17][C:18]1[CH:25]=[CH:24][C:21]([C:22]#N)=[CH:20][CH:19]=1)[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1.C([O:28]CC)C>O1CCCC1>[CH2:10]([S:17][C:18]1[CH:25]=[CH:24][C:21]([C:22]([C:3]2[CH:8]=[CH:7][C:6]([F:9])=[CH:5][CH:4]=2)=[O:28])=[CH:20][CH:19]=1)[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1

Participants

6

Reactant 4

HCID 3283Diethyl Ether2×HCID 99931-Bromo-4-fluorobenzeneHCID 8525724-(benzylthio)benzonitrileHCID 5462224Magnesium

Product 1

HCID 21262958HCID 21262958, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a suspension of 9.6 g of magnesium turnings in 20 ml of anhydrous diethyl ether is added dropwise a solution of 44 ml of 4-bromo-1-fluorobenzene in 300 ml of anhydrous diethyl ether. At the end of the addition, the mixture is stirred for a few minutes at room temperature and a solution of 46 g of 4-benzylthiobenzonitrile, prepared in example 16, in 400 ml of anhydrous tetrahydrofuran is added dropwise. The diethyl ether is distilled off and the mixture is heated under reflux for 3 hours before being cooled with ice. A 6M solution of hydrochloric acid (400 ml) is added dropwise and the mixture is heated under reflux for 6 hours. After the addition of water and dichloromethane, the organic phase is separated, dried over magnesium sulfate and evaporated in vacuo. The residue crystallizes in diisopropyl ether to give 48 g of 4-benzylthio-4'-fluorobenzophenone as crystals with a melting point of 96° C.

Workup

  1. additionAt the end of the addition
  2. additionis added dropwise
  3. distillationThe diethyl ether is distilled off
  4. temperaturethe mixture is heated
  5. temperatureunder reflux for 3 hours
  6. temperaturebefore being cooled with ice
  7. additionA 6M solution of hydrochloric acid (400 ml) is added dropwise
  8. temperaturethe mixture is heated
  9. temperatureunder reflux for 6 hours
  10. additionAfter the addition of water and dichloromethane
  11. customthe organic phase is separated
  12. dry with materialdried over magnesium sulfate
  13. customevaporated in vacuo
  14. customThe residue crystallizes in diisopropyl ether

Sources & evidence

ORD record
ord-ba1d82c5816c42918afd4f09f38559e6
Source dataset
uspto-grants-1998_11
Patent number
US05840753

Reaction notes

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