p-Bromoacetophenone → HCID 25023178, compound

HRID 626398Notes

Reaction equation

HRID 626398 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C:8](=O)[CH3:9])=[CH:4][CH:3]=1.[CH3:11][C:12]([S@@:15]([NH2:17])=[O:16])([CH3:14])[CH3:13]>C1COCC1.CC(O[Ti](OC(C)C)(OC(C)C)OC(C)C)C>[Br:1][C:2]1[CH:7]=[CH:6][C:5](/[C:8](=[N:17]/[S@:15]([C:12]([CH3:14])([CH3:13])[CH3:11])=[O:16])/[CH3:9])=[CH:4][CH:3]=1

Participants

5

Reactant 2

HCID 7466p-BromoacetophenoneHCID 11355477tert-Butylsulfinamide, (S)-(-)-

Product 1

HCID 25023178HCID 25023178, compound

Reagents, catalysts & solvents 2

HCID 178460666HCID 178460666, compoundCatalystHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 1-(4-bromophenyl)ethanone (2.0 g, 10 mmol) and (S)-2-methylpropane-2-sulfinamide (1.2 g, 10 mmol) in THF (20 mL) was added Ti(OiPr)4 (5 mL). The reaction mixture was refluxed overnight. The mixture was quenched with sat. NH4Cl solution and diluted with EtOAc. The mixture was filtered through a pad of Celite and washed with EtOAc. The layers were separated and the organic layer was washed with brine, dried and concentrated to give the titled compound.

Workup

  1. temperatureThe reaction mixture was refluxed overnight
  2. customThe mixture was quenched with sat. NH4Cl solution
  3. additiondiluted with EtOAc
  4. filtrationThe mixture was filtered through a pad of Celite
  5. washwashed with EtOAc
  6. customThe layers were separated
  7. washthe organic layer was washed with brine
  8. customdried
  9. concentrationconcentrated

Sources & evidence

ORD record
ord-5b135a80b1f840bd81e056ce9e18669c
Source dataset
uspto-grants-2016_04
Patent number
US09309227B2

Reaction notes

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