4-Bromo-1-ethyl-2-nitrobenzene → HCID 118362035, compound

HRID 2278404Notes

Reaction equation

HRID 2278404 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH3:9])=[C:4]([N+:10]([O-])=O)[CH:3]=1.[CH:13]([Mg]Br)=[CH2:14]>C1COCC1.O>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH3:9])=[C:4]2[C:3]=1[CH:13]=[CH:14][NH:10]2

Participants

5

Reactant 2

HCID 75669964-Bromo-1-ethyl-2-nitrobenzeneHCID 178418507HCID 178418507, compound

Product 1

HCID 118362035HCID 118362035, compoundYield 16.3%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-40 °C

Procedure

To a solution of 4-bromo-1-ethyl-2-nitro-benzene (8.7 g, 0.037 mol) in THF at −40° C. was added vinylmagnesium bromide (132 ml, 0.132 mol) dropwise, and the mixture was stirred at −40° C. for a further 2 h. The reaction mixture was diluted with water, extracted with EtOAc, dried over Na2SO4 and concentrated. The crude product was purified by silica gel column chromatography to afford the title compound (1.35 g, 16%).

Workup

  1. extractionextracted with EtOAc
  2. dry with materialdried over Na2SO4
  3. concentrationconcentrated
  4. customThe crude product was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-c7f1a3eb0f24449fbfe73062564f85f0
Source dataset
uspto-grants-2015_09
Patent number
US09133180B2

Reaction notes

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