Toluene → HCID 68516997, compound

HRID 732839Notes

Reaction equation

HRID 732839 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, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
110 °C

Procedure

Combine 2-(4-methanesulfonylphenyl)-6-methoxytetralone (1.0 eq.), hyflo (20%/weight), and toluene (7.5 volumes). Add PBr3 (1.5˜1.75 eq.) in one portion while stirring at room temperature. Heat contents to reflux (˜110° C.) overnight. Upon reaction completion, as judged by HPLC analysis (usually 15 hours), cool solution to 45° C. and slowly add 20 volumes THF. Stir for 30 minutes at 45° and filter warm over a pad of hyflo. The pad is washed with 2×2 volumes THF at 45° C. Concentrate filtrate to approximately 7 volumes. Add 7.5 volumes water to the remaining mixture keeping the temperature below 40° C. (NOTE: initial addition of water is very exothermic with large evolution of HBr). Cool slurry to room temperature and stir for 2 to 3 hours. Filter over a polypropylene pad and wash with 2×2 volumes water. Dry filter cake overnight at 60° C. under vacuum to give 1-bromo-2-(4-methanesulfonylphenyl)-3,4-dihydro-6-methoxynaphthalene.

Workup

  1. customUpon reaction completion
  2. customusually 15 hours
  3. temperaturecool solution to 45° C.
  4. filtrationfilter
  5. temperaturewarm over a pad of hyflo
  6. washThe pad is washed with 2×2 volumes THF at 45° C
  7. additionAdd 7.5 volumes water to the remaining mixture
  8. customthe temperature below 40° C.
  9. additioninitial addition of water
  10. temperatureCool slurry to room temperature
  11. stirringstir for 2 to 3 hours
  12. filtrationFilter over a polypropylene pad
  13. washwash with 2×2 volumes water
  14. customDry
  15. filtrationfilter cake overnight at 60° C. under vacuum

Sources & evidence

ORD record
ord-63b65e6881e549a493c4c867072a0d18
Source dataset
uspto-grants-2009_09
Patent number
US07585977B2

Reaction notes

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