Sulfuric acid magnesium salt (1:1) → HCID 88539500, compound

HRID 1404564Notes

Reaction equation

HRID 1404564 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 88539500HCID 88539500, compoundYield 44.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of (S)-2-methylpropane-2-sulfinamide (4 g, 33.0 mmol) and 4-bromo-2-fluorobenzaldehyde (7.03 g, 34.7 mmol) in DCM (80.0 ml) were added pyridinium p-toluenesulfonate (415 mg, 1.65 mmol) and magnesium sulfate (39.7 g, 330 mmol) and the reaction mixture was stirred at room temperature over night. Then additional magnesium sulfate (19.85 g, 165 mmol) was added and stirring was continued for 24 h. The reaction mixture was filtered through a pad of celite and the filtrate was evaporated. The remaining light yellow oil was purified by chromatography (silica gel; heptane/EtOAc 95:5-90:10) to obtain the title compound as colorless oil (4.5 g, 44%).

Workup

  1. stirringstirring
  2. filtrationThe reaction mixture was filtered through a pad of celite
  3. customthe filtrate was evaporated
  4. customThe remaining light yellow oil was purified by chromatography (silica gel; heptane/EtOAc 95:5-90:10)

Sources & evidence

ORD record
ord-4ad2423bf59d41f3a9c9e3c9be0f4202
Source dataset
uspto-grants-2014_12
Patent number
US08912221B2

Reaction notes

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