p-Toluenesulfonic acid → HCID 88003152, compound

HRID 2086704Notes

Reaction equation

HRID 2086704 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C:8](=[O:13])[CH2:9][N+:10]([O-:12])=[O:11])=[CH:4][CH:3]=1.CO[CH:16](OC)[N:17]([CH3:19])[CH3:18].CC1C=CC(S(O)(=O)=O)=CC=1>C1COCC1>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C:8](=[O:13])/[C:9](/[N+:10]([O-:12])=[O:11])=[CH:16]\[N:17]([CH3:19])[CH3:18])=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 6101p-Toluenesulfonic acidHCID 78373Dimethylformamide dimethyl acetalHCID 12388011HCID 12388011, compound

Product 1

HCID 88003152HCID 88003152, compoundYield 43%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 1-(4-bromophenyl)-2-nitroethanone (5.38 g, 0.022 mol, Seter J. et al., Isr. J. Chem., 4, 7 (1966)) and N,N-dimethylformamide dimethylacetal (2.9 g, 0.024 mol) and catalitic amount of p-TsOH in THF (100 mL) was refluxed for 10 h. The mixture was cooled to room temperature and concentrated in vacuo. The reaction mixture was purified by flash chromatography eluting with ethyl acetate/hexane (1/1) to give title compound (2.8 g, 43%).

Workup

  1. temperaturewas refluxed for 10 h
  2. concentrationconcentrated in vacuo
  3. customThe reaction mixture was purified by flash chromatography
  4. washeluting with ethyl acetate/hexane (1/1)

Sources & evidence

ORD record
ord-289bbb5e250c43b5b5538fd37a1ddb70
Source dataset
uspto-grants-2004_04
Patent number
US06727238B2

Reaction notes

Loading…