HCID 16102910, compound → HCID 68454599, compound

HRID 896717Notes

Reaction equation

HRID 896717 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5](/[CH:8]=[N:9]/[S:10]([C:12]([CH3:15])([CH3:14])[CH3:13])=[O:11])=[C:4]([F:16])[CH:3]=1.[CH3:17][Mg]Cl>C(Cl)Cl>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C@H:8]([NH:9][S:10]([C:12]([CH3:13])([CH3:15])[CH3:14])=[O:11])[CH3:17])=[C:4]([F:16])[CH:3]=1

Participants

4

Reactant 2

HCID 16102910HCID 16102910, compoundHCID 178418332HCID 178418332, compound

Product 1

HCID 68454599HCID 68454599, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of N-[(1E)-(4-bromo-2-fluorophenyl)methylidene]-2-methylpropane-2-sulfinamide (32.65 g, 0.1066 mol) in 550 mL CH2Cl2 at −48° C. was added methylmagnesium chloride (3.0 M solution is ether, 53.31 mL, 0.1599 mol) dropwise. The reaction was quenched with aqueous ammonium chloride and the aqueous layer was extracted with methylene chloride. The combined organics were dried over Na2SO4, filtered and concentrated under vacuum. The resulting residue was subjected to column chromatography on silica gel eluted with 10-50% ethyl acetate in hexanes to afford N-[(1R)-1-(4-bromo-2-fluorophenyl)ethyl]-2-methylpropane-2-sulfinamide as a white solid that gave proton NMR spectra consistent with theory and a mass ion (ES+) of 324.14 for M+H+ (81Br).

Workup

  1. customThe reaction was quenched with aqueous ammonium chloride
  2. extractionthe aqueous layer was extracted with methylene chloride
  3. dry with materialThe combined organics were dried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated under vacuum
  6. washeluted with 10-50% ethyl acetate in hexanes

Sources & evidence

ORD record
ord-2a24f93d4b6f4be8b310ccace84adb1a
Source dataset
uspto-grants-2005_07
Patent number
US06919343B2

Reaction notes

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