tert-Butylsulfinamide, (S)-(-)- → HCID 118045320, compound

HRID 596003Notes

Reaction equation

HRID 596003 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([CH:7]=[C:8]([F:10])[CH:9]=1)[CH:5]=O.[CH3:11][C:12]([S@@:15]([NH2:17])=[O:16])([CH3:14])[CH3:13]>ClCCCl.S([O-])([O-])(=O)=O.[Cu+2]>[Br:1][C:2]1[CH:3]=[C:4]([CH:7]=[C:8]([F:10])[CH:9]=1)/[CH:5]=[N:17]/[S@:15]([C:12]([CH3:14])([CH3:13])[CH3:11])=[O:16]

Participants

5

Reactant 2

HCID 11355477tert-Butylsulfinamide, (S)-(-)-HCID 219862463-Bromo-5-fluorobenzaldehyde

Product 1

HCID 118045320HCID 118045320, compoundYield 99.4%

Reagents, catalysts & solvents 2

HCID 24462Copper SulfateCatalystHCID 111,2-DichloroethaneSolvent

Conditions

Temperature
60 °C

Procedure

To a solution of 3-bromo-5-fluorobenzaldehyde (5 g, 24.63 mmol) and (S)-2-methylpropane-2-sulfinamide (3.28 g, 27.1 mmol) in DCE (82 mL) was added copper(II) sulfate (anhydrous) (7.86 g, 49.3 mmol). The suspension was stirred under nitrogen at 60° C. overnight. The reaction mixture was cooled down, filtered through a plug of celite, and rinsed with DCM. The filtrate was concentrated to yield the crude product. The crude product was purified by flash chromatograph eluting with 0-30% EtOAc in heptane to yield the product (S,E)-N-(3-bromo-5-fluorobenzylidene)-2-methylpropane-2-sulfinamide (7.5 g, 24.49 mmol, 99% yield) as a light yellow color oil. LCMS (m/z): 306.1/308.1 (MH+), 1.04 min.

Workup

  1. temperatureThe reaction mixture was cooled down
  2. filtrationfiltered through a plug of celite
  3. washrinsed with DCM
  4. concentrationThe filtrate was concentrated
  5. customto yield the crude product
  6. customThe crude product was purified by flash chromatograph
  7. washeluting with 0-30% EtOAc in heptane

Sources & evidence

ORD record
ord-51693e601ff34f6eb4acbfbcc2155695
Source dataset
uspto-grants-2016_01
Patent number
US09242996B2

Reaction notes

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