4-Bromo-2-fluorotoluene → HCID 54058293, compound

HRID 2293291Notes

Reaction equation

HRID 2293291 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([CH3:8])=[C:4]([F:9])[CH:3]=1.[Mg].[CH2:11]([S:18]C1C=CC(C#N)=CC=1)[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1>C(OCC)C.O1CCCC1>[F:9][C:4]1[CH:3]=[C:2]([CH:7]=[CH:6][C:5]=1[CH3:8])[C:11]([C:12]1[CH:13]=[CH:14][C:15]([CH2:8][C:5]2[CH:6]=[CH:7][CH:2]=[CH:3][CH:4]=2)=[CH:16][CH:17]=1)=[S:18]

Participants

6

Reactant 3

HCID 1710404-Bromo-2-fluorotolueneHCID 8525724-(benzylthio)benzonitrileHCID 5462224Magnesium

Product 1

HCID 54058293HCID 54058293, compoundYield 77.9%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolvent2×HCID 8028TetrahydrofuranSolvent

Procedure

A solution of 95 g (500 mmol) of 4-bromo-2-fluorotoluene in 200 ml of anhydrous ethyl ether is added dropwise to a suspension of 12.2 g (500 mmol) of magnesium turnings covered with anhydrous ethyl ether. When the addition has ended, the mixture is stirred for 30 minutes at room temperature and a solution of 50 g of 4-(benzylthio)benzonitrile in 200 ml of anhydrous tetrahydrofuran is then added dropwise. The ethyl ether is distilled and the mixture is refluxed for 6 hours. After cooling, the mixture is run dropwise into 600 ml of 6N hydrochloric acid solution and the resulting solution is refluxed for 6 hours. After the addition of isopropyl ether, the crystals formed are filtered off and washed with ethanol and then with ethyl ether to give 55.4 g of 3-fluoro-4-methyl-4'-benzylthiobenzophenone in the form of crystals melting at 122° C.

Workup

  1. additionWhen the addition
  2. distillationThe ethyl ether is distilled
  3. temperaturethe mixture is refluxed for 6 hours
  4. temperatureAfter cooling
  5. temperaturethe resulting solution is refluxed for 6 hours
  6. additionAfter the addition of isopropyl ether
  7. customthe crystals formed
  8. filtrationare filtered off
  9. washwashed with ethanol

Sources & evidence

ORD record
ord-fea594da07c843fba9cb353bc865d562
Source dataset
uspto-grants-1997_11
Patent number
US05686460

Reaction notes

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