Water → 1-Bromo-4-[(trans)-2-nitrocyclopropyl]benzene

HRID 1844236Notes

Reaction equation

HRID 1844236 reaction equation
[I-].C[S+](C)(C)=O.[CH3:7]C([O-])(C)C.[K+].[Br:13][C:14]1[CH:19]=[CH:18][C:17](/[CH:20]=[CH:21]/[N+:22]([O-:24])=[O:23])=[CH:16][CH:15]=1.O>CS(C)=O>[Br:13][C:14]1[CH:15]=[CH:16][C:17]([C@@H:20]2[CH2:7][C@H:21]2[N+:22]([O-:24])=[O:23])=[CH:18][CH:19]=1

Participants

6

Reactant 4

HCID 962WaterHCID 74498Sulfoxonium, trimethyl-, iodide (1:1)HCID 688204trans-4-Bromo-beta-nitrostyreneHCID 23665647Potassium tert-butoxide

Product 1

HCID 670646391-Bromo-4-[(trans)-2-nitrocyclopropyl]benzeneYield 27%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent2×

Procedure

Trimethylsulfoxonium iodide (0.62 g, 2.82 mmol) was added in portions to a solution of t-BuOK (0.32 g, 2.82 mmol) in dry DMSO (5 mL). After 10 min a solution of 1-bromo-4-[(trans)-2-nitrovinyl]benzene (0.53 g, 2.35 mmol) in DMSO (5 mL) was transferred via canula and the mixture was stirred at room temperature for 6 h. The reaction was poured over water (10 mL) and extracted with Et2O (3×10 mL); the organic layers were washed with brine (2×15 mL), dried over anhydrous Na2SO4 and filtered. After removal of the solvent, the residual oil was purified by column chromatography on silica gel (5% EtOAc/hexanes) affording 0.15 of 1-bromo-4-[(trans)-2-nitrocyclopropyl]benzene [27% yield].

Workup

  1. extractionextracted with Et2O (3×10 mL)
  2. washthe organic layers were washed with brine (2×15 mL)
  3. dry with materialdried over anhydrous Na2SO4
  4. filtrationfiltered
  5. customAfter removal of the solvent
  6. customthe residual oil was purified by column chromatography on silica gel (5% EtOAc/hexanes)

Sources & evidence

ORD record
ord-bf0e34c50e5441799b393716139565b7
Source dataset
uspto-grants-2015_02
Patent number
US08946296B2

Reaction notes

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