Potassium bis(trimethylsilyl)amide → 1-Cyclopropanesulfonyl-2,3,4-trifluoro-benzene

HRID 2251265Notes

Reaction equation

HRID 2251265 reaction equation
Cl[CH2:2][CH2:3][CH2:4][S:5]([C:8]1[CH:13]=[CH:12][C:11]([F:14])=[C:10]([F:15])[C:9]=1[F:16])(=[O:7])=[O:6].C[Si]([N-][Si](C)(C)C)(C)C.[K+]>C1COCC1>[CH:4]1([S:5]([C:8]2[CH:13]=[CH:12][C:11]([F:14])=[C:10]([F:15])[C:9]=2[F:16])(=[O:7])=[O:6])[CH2:2][CH2:3]1

Participants

4

Reactant 2

HCID 3251421Potassium bis(trimethylsilyl)amideHCID 69036753HCID 69036753, compound

Product 1

HCID 690384121-Cyclopropanesulfonyl-2,3,4-trifluoro-benzene

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To 5.9 mmol 1-(3-chloro-propane-1-sulfonyl)-2,3,4-trifluoro-benzene in 200 ml THF at −78° C. was added dropwise over 30 min 7.0 mmol of a 0.9 M solution of potassium bis(trimethylsilyl)amide in THF. The reaction mixture was then allowed to warm to RT, and stirring continued for a further 30 min at RT. The mixture was then quenched by addition of 1 M aq HCl and extracted three times with ethyl acetate. The combined organic phases were dried with Na2SO4, and concentrated in vacuo. The residue was chromatographed on silica gel (eluant: ethyl acetate/heptane 1:4) to afford the title compound. MS (m/e): 237.2 (M+H+, 100%)

Workup

  1. customThe mixture was then quenched by addition of 1 M aq HCl
  2. extractionextracted three times with ethyl acetate
  3. dry with materialThe combined organic phases were dried with Na2SO4
  4. concentrationconcentrated in vacuo
  5. customThe residue was chromatographed on silica gel (eluant: ethyl acetate/heptane 1:4)

Sources & evidence

ORD record
ord-b524b19aac8143be929f58c4437fcc89
Source dataset
uspto-grants-2008_01
Patent number
US07319099B2

Reaction notes

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