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

HRID 513036

反応式

HRID 513036 の反応式
[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]

参加物

7

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 3

HCID 76524Titanium tetraethoxide触媒HCID 8028Tetrahydrofuran溶媒HCID 57417360Sodium chloride; water溶媒

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-8f93c56bdba74f41ac6dde8bcd2037e1
出典データセット
uspto-grants-2015_08
特許番号
US09102671B2

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