3'-Bromoacetophenone → HCID 86666428, compound

HRID 1042077Notes

Reaction equation

HRID 1042077 reaction equation
[CH3:1][C:2]([S@:5]([NH2:7])=[O:6])([CH3:4])[CH3:3].[Br:8][C:9]1[CH:10]=[C:11]([C:15](=O)[CH3:16])[CH:12]=[CH:13][CH:14]=1>C1COCC1.[Cl-].[Na+].O>[Br:8][C:9]1[CH:10]=[C:11]([C:15](=[N:7][S@@:5]([C:2]([CH3:4])([CH3:3])[CH3:1])=[O:6])[CH3:16])[CH:12]=[CH:13][CH:14]=1

Participants

5

Reactant 2

HCID 165023'-BromoacetophenoneHCID 10964479tert-Butylsulfinamide, (R)-(+)-

Product 1

HCID 86666428HCID 86666428, compound

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 57417360Sodium chloride; waterSolvent

Conditions

Temperature
70 °C

Procedure

Add Ti(OEt)4 (7 mL, 17 mmol) to a solution of (R)-(+)-2-methyl-2-propane sulfinamide (1.0 g, 8.3 mmol) and 1-(3-bromophenyl)ethanone (1.8 g, 9.1 mmol) in anhydrous THF (30 mL) at RT. Heat the mixture at 70° C. for 24 h. Allow the reaction mixture to cool to RT and pour into 30 mL of brine under vigorous stirring. Filter the suspension through a pad of Celite and wash the solid with EtOAc (2×20 mL). Wash the filtrate with brine (30 mL), dry (Na2SO4), and concentrate in vacuo. Chromatograph the residue on a silica gel column and elute with Et2O/hexanes to give (R)—N-(1-(3-bromophenyl)ethylidene)-2-methylpropane-2-sulfinamide.

Workup

  1. temperatureto cool to RT
  2. filtrationFilter the suspension through a pad of Celite
  3. washwash the solid with EtOAc (2×20 mL)
  4. washWash the filtrate with brine (30 mL)
  5. dry with materialdry (Na2SO4)
  6. concentrationconcentrate in vacuo
  7. washChromatograph the residue on a silica gel column and elute with Et2O/hexanes

Sources & evidence

ORD record
ord-f34cdd1cd06a43049da29886b3b0dff9
Source dataset
uspto-grants-2013_10
Patent number
US08557826B2

Reaction notes

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