Sulfuric acid magnesium salt (1:1) → HCID 16102910, compound

HRID 896716Notes

Reaction equation

HRID 896716 reaction equation
[CH3:1][C:2]([S@@:5]([NH2:7])=[O:6])([CH3:4])[CH3:3].[Br:8][C:9]1[CH:16]=[CH:15][C:12]([CH:13]=O)=[C:11]([F:17])[CH:10]=1.C1(C)C=CC(S([O-])(=O)=O)=CC=1.[NH+]1C=CC=CC=1.S([O-])([O-])(=O)=O.[Mg+2]>C(Cl)Cl>[Br:8][C:9]1[CH:16]=[CH:15][C:12](/[CH:13]=[N:7]/[S:5]([C:2]([CH3:4])([CH3:3])[CH3:1])=[O:6])=[C:11]([F:17])[CH:10]=1

Participants

6

Reactant 4

HCID 24083Sulfuric acid magnesium salt (1:1)2×HCID 1435174-Bromo-2-fluorobenzaldehydeHCID 466102Benzenesulfonic acid, 4-methyl-, compd. with pyridine (1:1)HCID 11355477tert-Butylsulfinamide, (S)-(-)-

Product 1

HCID 16102910HCID 16102910, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of (S)-(−)-2-methyl-2-propanesulfinamide (20.20 g, 0.167 mol) in 350 mL CH2Cl2 were added 4-bromo-2-fluorobenzaldehyde (35.53 g, 0.1750 mol), pyridinium-p-toluenesulfonate (2.09 g, 8.33 mmol), and magnesium sulfate (200.6 g, 1.667 mol). The reaction mixture was stirred at room temperature for 48 hours. Additional magnesium sulfate (100.3 g, 0.833 mol) was added, and the reaction was stirred 24 hours. The mixture was filtered through celite, washing with CH2Cl2 and concentrated in vacuo. The resulting residue was subjected to column chromatography on silica gel eluted with 0-10% ethyl acetate in hexanes to afford N-[(1E)-(4-bromo-2-fluorophenyl)methylidene]-2-methylpropane-2-sulfinamide as a white solid that gave proton NMR spectra consistent with theory and a mass ion (ES+) of 308.09 for M+H+ (81Br).

Workup

  1. stirringthe reaction was stirred 24 hours
  2. filtrationThe mixture was filtered through celite
  3. washwashing with CH2Cl2
  4. concentrationconcentrated in vacuo
  5. washeluted with 0-10% ethyl acetate in hexanes

Sources & evidence

ORD record
ord-828d4fb78c7e4676baf41950b3967d45
Source dataset
uspto-grants-2005_07
Patent number
US06919343B2

Reaction notes

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