(Trifluoromethyl)trimethylsilane → HCID 66999612, compound

HRID 558162Notes

Reaction equation

HRID 558162 reaction equation
[Br:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1/[C:9](=[N:11]/[S@:12]([C:14]([CH3:17])([CH3:16])[CH3:15])=[O:13])/C.[F:18][C:19]([Si](C)(C)C)([F:21])[F:20]>C1COCC1>[Br:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[C@@H:9]([NH:11][S@:12]([C:14]([CH3:17])([CH3:16])[CH3:15])=[O:13])[C:19]([F:21])([F:20])[F:18]

Participants

4

Reactant 2

HCID 552549(Trifluoromethyl)trimethylsilaneHCID 87231630HCID 87231630, compound

Product 1

HCID 66999612HCID 66999612, compoundYield 91%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-60 °C

Procedure

Add tetrabutylammonium triphenyldifluorosilicate (29.8 g, 55.19 mmol) to a stirring mixture of (S,E)-N-(1-(2-bromo-4-fluorophenyl)ethylidene)-2-methylpropane-2-sulfinamide (13 g, 42.46 mmol) in THF. Cool the mixture to about −60° C. and add the (trifluoromethyl)trimethylsilane over about 10 min. Warm up to −55° C. and stir for 2 h. Continue to warm up to 0° C. Cool the mixture back to −30° C., and quench with saturated NH4Cl (150 mL). Extract product into ethyl acetate (2×200 mL). Combine extracts, wash with aqueous saturated sodium chloride, dry over Na2SO4, filter, and concentrate. Purify the material on 700 g silica eluting with 8:2 to 1:1 hexanes:ethyl acetate to a crude material. Crystallize the material to give long needles (9.7 g, 91%). MS (ES) m/z 377 [M+1]+.

Workup

  1. temperatureWarm up to −55° C.
  2. temperatureto warm up to 0° C
  3. temperatureCool the mixture back to −30° C.
  4. customquench with saturated NH4Cl (150 mL)
  5. washCombine extracts, wash with aqueous saturated sodium chloride
  6. dry with materialdry over Na2SO4
  7. filtrationfilter
  8. concentrationconcentrate
  9. customPurify the material on 700 g silica eluting with 8:2 to 1:1 hexanes
  10. customCrystallize the material

Sources & evidence

ORD record
ord-3e424ed68af74ec0856fe09ba9d8a77b
Source dataset
uspto-grants-2011_11
Patent number
US08063035B2

Reaction notes

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