Ethyl Acetate → (NE,S)-N-[(2-bromo-5-fluorophenyl)methylidene]-2-methylpropane-2-sulfinamide

HRID 513036

Reaktionsgleichung

Reaktionsgleichung von HRID 513036
[Br:1][C:2]1[CH:9]=[CH:8][C:7]([F:10])=[CH:6][C:3]=1[CH:4]=O.[CH3:11][C:12]([S@@:15]([NH2:17])=[O:16])([CH3:14])[CH3:13].CCOC(C)=O>C1COCC1.[Cl-].[Na+].O.[O-]CC.[O-]CC.[O-]CC.[O-]CC.[Ti+4]>[Br:1][C:2]1[CH:9]=[CH:8][C:7]([F:10])=[CH:6][C:3]=1/[CH:4]=[N:17]/[S@:15]([C:12]([CH3:14])([CH3:13])[CH3:11])=[O:16]

Komponenten

7

Edukt 3

HCID 8857Ethyl AcetateHCID 27733212-Bromo-5-fluorobenzaldehydeHCID 11355477tert-Butylsulfinamide, (S)-(-)-

Produkt 1

HCID 71725992(NE,S)-N-[(2-bromo-5-fluorophenyl)methylidene]-2-methylpropane-2-sulfinamide

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 76524Titanium tetraethoxideKatalysatorHCID 8028TetrahydrofuranLösungsmittelHCID 57417360Sodium chloride; waterLösungsmittel

Versuchsvorschrift

To a solution of 2-bromo-5-fluorobenzaldehyde (2.44 g, 12.0 mmol) and (S)-(−)-2-methyl-2-propane-sulfinamide (1.45 g, 12.0 mmol) in THF (30 mL, anhyd.) was added titanium tetraethoxide (2.8 mL, 13.2 mmol, tech) at room temperature. After stirring 16 hours the reaction mixture was charged with brine (25 mL) and EtOAc (40 mL). After stirring 10 minutes the mixture was filtered through a pad of Celite™. Combined filtrates were washed with water and brine, dried over sodium sulfate and concentrated. The residue was purified by silica chromatography with EtOAc/Hex (0-25%) as eluent to give (S,E)-N-(2-bromo-5-fluorobenzylidene)-2-methylpropane-2-sulfinamide (I-44) as a white solid. 1H NMR (400 MHz, CDCl3) δ 8.94 (d, J=2.2 Hz, 1 H), 7.77 (dd, J=3.1, 9.1 Hz, 1 H), 7.64 (dd, J=5.0, 8.8 Hz, 1 H), 7.12 (ddd, J=3.1, 7.5, 8.8 Hz, 1 H), 1.30 (s, 9 H).

Aufarbeitung

  1. stirringAfter stirring 10 minutes the mixture
  2. filtrationwas filtered through a pad of Celite™
  3. washCombined filtrates were washed with water and brine
  4. dry with materialdried over sodium sulfate
  5. concentrationconcentrated
  6. customThe residue was purified by silica chromatography with EtOAc/Hex (0-25%) as eluent

Quellen und Nachweise

ORD-Eintrag
ord-8f93c56bdba74f41ac6dde8bcd2037e1
Quelldatensatz
uspto-grants-2015_08
Patentnummer
US09102671B2

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