(Trifluoromethyl)trimethylsilane → (R)-N-((S)-1-(4-bromo-2-chlorophenyl)-2,2,2-trifluoroethyl)-2-methylpropane-2-sulfinamide

HRID 1511368

Reaction equation

HRID 1511368 reaction equation
[Br:1][C:2]1[CH:15]=[CH:14][C:5](/[CH:6]=[N:7]\[S@@:8]([C:10]([CH3:13])([CH3:12])[CH3:11])=[O:9])=[C:4]([Cl:16])[CH:3]=1.[F:17][C:18]([Si](C)(C)C)([F:20])[F:19]>CN(C=O)C>[Br:1][C:2]1[CH:15]=[CH:14][C:5]([C@H:6]([NH:7][S@@:8]([C:10]([CH3:12])([CH3:13])[CH3:11])=[O:9])[C:18]([F:20])([F:19])[F:17])=[C:4]([Cl:16])[CH:3]=1

Participants

4

Reactant 2

HCID 552549(Trifluoromethyl)trimethylsilaneHCID 57691068(NZ,R)-N-[(4-bromo-2-chlorophenyl)methylidene]-2-methylpropane-2-sulfinamide

Product 1

HCID 57691004(R)-N-((S)-1-(4-bromo-2-chlorophenyl)-2,2,2-trifluoroethyl)-2-methylpropane-2-sulfinamide

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
35 °C

Procedure

To a stirring solution of (R,Z)—N-(4-bromo-2-chlorobenzylidene)-2-methylpropane-2-sulfinamide (1370 mg, 4246 μmol) and (trifluoromethyl)trimethylsilane (943 μl, 6369 μmol) in DMF (5 mL) was added 1,3-bis(1-adamantyl)imidazol-2-ylidene (143 mg, 425 μmol). Reaction stirred at 35° C. for 18 h then quenched with sat NH4Cl (10 mL). Reaction partitioned between EtOAc (40 mL) and 5% NaHCO3 (10 mL). Organic dried over MgSO4, concentrated to and oil from toluene, then purified on silica (80 g) eluting with 20>30% EtOAc/Hex. Product isolated as a white solid.

Workup

  1. customReaction
  2. customthen quenched with sat NH4Cl (10 mL)
  3. customReaction
  4. custompartitioned between EtOAc (40 mL) and 5% NaHCO3 (10 mL)
  5. dry with materialOrganic dried over MgSO4
  6. concentrationconcentrated to and oil from toluene
  7. custompurified on silica (80 g)
  8. washeluting with 20>30% EtOAc/Hex
  9. customProduct isolated as a white solid

Sources & evidence

ORD record
ord-0e586812655441979c84f2328da396a2
Source dataset
uspto-grants-2012_07
Patent number
US08212041B2

Linked notes

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