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

HRID 2251255Notes

Reaction equation

HRID 2251255 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])[CH:9]=1)(=[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])[CH:9]=2)(=[O:7])=[O:6])[CH2:2][CH2:3]1

Participants

4

Reactant 2

HCID 3251421Potassium bis(trimethylsilyl)amideHCID 43345129HCID 43345129, compound

Product 1

HCID 690421904-Cyclopropanesulfonyl-1,2-difluoro-benzene

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To 11.8 mmol 4-(3-chloro-propane-1-sulfonyl)-1,2-difluoro-benzene in 400 ml THF at −78° C. was added dropwise over 30 min 14.2 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 1:5) to afford the title compound. MS (m/e): 219.2 (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 1:5)

Sources & evidence

ORD record
ord-cb761123a62f40baa333a476ed58ce88
Source dataset
uspto-grants-2008_01
Patent number
US07319099B2

Reaction notes

Loading…