Toluene → HCID 68516997, compound

HRID 748972Notes

Reaction equation

HRID 748972 reaction equation
[CH3:1][S:2]([C:5]1[CH:10]=[CH:9][C:8]([CH:11]2[CH2:20][CH2:19][C:18]3[C:13](=[CH:14][CH:15]=[C:16]([O:21][CH3:22])[CH:17]=3)[C:12]2=O)=[CH:7][CH:6]=1)(=[O:4])=[O:3].C1(C)C=CC=CC=1.P(Br)(Br)[Br:32]>C1COCC1>[Br:32][C:12]1[C:13]2[C:18](=[CH:17][C:16]([O:21][CH3:22])=[CH:15][CH:14]=2)[CH2:19][CH2:20][C:11]=1[C:8]1[CH:9]=[CH:10][C:5]([S:2]([CH3:1])(=[O:4])=[O:3])=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 1140TolueneHCID 24614Phosphorus tribromideHCID 685187843,4-Dihydro-6-methoxy-2-[4-(methylsulfonyl)phenyl]-1(2H)-naphthalenone

Product 1

HCID 68516997HCID 68516997, compoundYield 74%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Add 2-(4-methanesulfonyl-phenyl)-6-methoxy-3,4-dihydro-2H-naphthalen-1-one (1.0 eq.), hyflo (20 wt %), and toluene (7.5 vols) to a three neck flask with a reflux condenser and nitrogen vent purge. While stirring at room temperature, add PBr3 (1.75 eq.) in one portion. Heat the reaction to reflux (˜110° C.) overnight allowing it to vent through a caustic scrubber. After refluxing for 15 hours, cool the yellow solution to 45° C. and slowly add THF (20 vols). Stir this mixture for 30 minutes at 45° and filter it, while warm, over a pad of Hyflo. Wash the pad with 45° C. THF (2×2 vols). Concentrate the filtrate at reduced pressure to remove all of the THF. Carefully add water (7.5 vols) to the remaining mixture keeping the temperature below 40° C. Cool the slurry to room temperature and stir it for 2 to 3 hours. Filter the slurry over a polypropylene pad and wash it with water (2×2 vols). Dry the resulting filter cake in a vacuum oven overnight at 50° C. to provide the title compound (74%).

Workup

  1. customnitrogen vent purge
  2. temperatureHeat
  3. customthe reaction
  4. temperatureto reflux (˜110° C.) overnight
  5. temperatureAfter refluxing for 15 hours
  6. temperaturecool the yellow solution to 45° C.
  7. stirringStir this mixture for 30 minutes at 45°
  8. filtrationfilter it
  9. temperaturewhile warm, over a pad of Hyflo
  10. washWash the pad with 45° C
  11. concentrationConcentrate the filtrate at reduced pressure
  12. customto remove all of the THF
  13. customthe temperature below 40° C
  14. temperatureCool the slurry to room temperature
  15. stirringstir it for 2 to 3 hours
  16. filtrationFilter the slurry over a polypropylene pad
  17. washwash it with water (2×2 vols)
  18. customDry the resulting
  19. filtrationfilter cake in a vacuum oven overnight at 50° C.

Sources & evidence

ORD record
ord-68830429961748b881a737b57aba3cab
Source dataset
uspto-grants-2008_07
Patent number
US07399867B2

Reaction notes

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