Tetrahydrofuran → 2-Methyl-propane-2-sulfonic acid 4-bromo-3-fluoro-benzylideneamide

HRID 1617320Notes

Reaction equation

HRID 1617320 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)=[CH:11][C:10]=1[F:17].C1C[O:21]CC1>[Cl-].[Na+].O.[O-]CC.[Ti+4].[O-]CC.[O-]CC.[O-]CC>[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:21])=[O:6])=[CH:11][C:10]=1[F:17]

Participants

6

Reactant 3

HCID 8028TetrahydrofuranHCID 27834114-Bromo-3-fluorobenzaldehydeHCID 3382465Tert-Butanesulfinamide

Product 1

HCID 866885562-Methyl-propane-2-sulfonic acid 4-bromo-3-fluoro-benzylideneamide

Reagents, catalysts & solvents 2

HCID 76524Titanium tetraethoxideCatalystHCID 57417360Sodium chloride; waterSolvent

Procedure

11.1 g (91.0 mmol) 2-Methyl-2-propanesulfinamide are added to 16.5 g (76.0 mmol) 4-bromo-3-fluoro-benzaldehyde and 34.6 g (152 mmol) titanium(IV) ethoxide in 100 mL THF. Stirring is continued for 1.5 h at 50° C. After that time, the mixture is poured into brine. The mixture is filtered over celite and the filtrate is transferred to a separation funnel. The organic layer is separated, dried over magnesium sulphate and the solvent is removed by evaporation. The residue is purified by column chromatography (silica gel; gradient hexane/EtOAc 1:0→3:2) to yield the desired product.

Workup

  1. filtrationThe mixture is filtered over celite
  2. customthe filtrate is transferred to a separation funnel
  3. customThe organic layer is separated
  4. dry with materialdried over magnesium sulphate
  5. customthe solvent is removed by evaporation
  6. customThe residue is purified by column chromatography (silica gel; gradient hexane/EtOAc 1:0→3:2)

Sources & evidence

ORD record
ord-dc4432da03e244d5a32238de584a6647
Source dataset
uspto-grants-2014_07
Patent number
US08765959B2

Reaction notes

Loading…