Diethyl Ether → HCID 21262958, compound

HRID 568076Notes

Reaction equation

HRID 568076 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([F:8])=[CH:4][CH:3]=1.[Mg].[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:2]2[CH:7]=[CH:6][C:5]([F:8])=[CH:4][CH:3]=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

A solution of 44 ml of 4-bromo-1-fluorobenzene in 300 ml of anhydrous diethyl ether is added dropwise to a suspension of 9.6 g of magnesium turnings in 20 ml of anhydrous diethyl ether. When the addition is complete, the mixture is stirred for a few minutes at room temperature and a solution of 46 g of 4-benzylthiobenzonitrile, prepared in Example 55, in 400 ml of anhydrous tetrahydrofuran is added dropwise. The diethyl ether is distilled and the mixture is refluxed for 3 hours and then cooled with ice. 6 N hydrochloric acid solution (400 ml) is added dropwise and the mixture is refluxed for 6 hours. After the addition of water and dichloromethane, the organic phase is decanted, dried over magnesium sulphate and then evaporated under vacuum. The residue crystallises from diisopropyl ether to give 48 g of 4-benzylthio-4′-fluorobenzophenone in the form of crystals melting at 96° C.

Workup

  1. additionWhen the addition
  2. additionis added dropwise
  3. distillationThe diethyl ether is distilled
  4. temperaturethe mixture is refluxed for 3 hours
  5. temperaturecooled with ice
  6. addition6 N hydrochloric acid solution (400 ml) is added dropwise
  7. temperaturethe mixture is refluxed for 6 hours
  8. additionAfter the addition of water and dichloromethane
  9. customthe organic phase is decanted
  10. dry with materialdried over magnesium sulphate
  11. customevaporated under vacuum
  12. customThe residue crystallises from diisopropyl ether

Sources & evidence

ORD record
ord-fc53869c2c65476eb7ed2c4c3cabc499
Source dataset
uspto-grants-2001_01
Patent number
US06180651B2

Reaction notes

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