Benzene, 1-ethyl-4-nitro- → 1-(1-Bromoethyl)-4-nitrobenzene

HRID 601019Notes

Reaction equation

HRID 601019 reaction equation
[CH2:1]([C:3]1[CH:8]=[CH:7][C:6]([N+:9]([O-:11])=[O:10])=[CH:5][CH:4]=1)[CH3:2].[Br:12]N1C(=O)CCC1=O>C(Cl)(Cl)(Cl)Cl.C(OOC(=O)C1C=CC=CC=1)(=O)C1C=CC=CC=1>[Br:12][CH:1]([C:3]1[CH:4]=[CH:5][C:6]([N+:9]([O-:11])=[O:10])=[CH:7][CH:8]=1)[CH3:2]

Participants

5

Reactant 2

HCID 7480Benzene, 1-ethyl-4-nitro-HCID 67184N-bromobutanimide

Product 1

HCID 110206791-(1-Bromoethyl)-4-nitrobenzeneYield 91.5%

Reagents, catalysts & solvents 2

HCID 7187Benzoyl PeroxideCatalystHCID 5943Carbon TetrachlorideSolvent

Procedure

A mixture of 1-ethyl-4-nitro-benzene (3.4 mL, 25 mmol), N-bromosuccinimide (4.38 g, 24.6 mmol) and benzoylperoxide (0.04 g, 0.18 mmol) in carbon tetrachloride (30 mL) was refluxed 1 h, cooled and filtered, washing with 1:1 ethyl acetate:hexanes. The filtrate was evaporated and purified by flash chromatography (SiO2) eluted with 2:98 ethyl acetate:hexanes to provide 1-(1-bromo-ethyl)-4-nitro-benzene (5.18 g, 90% yield) as a yellow oil. 1H-NMR (CDCl3, 500 MHz) 8.22 (d, 2H), 7.62 (d, 2H), 5.22 (q, 1H), 2.08 (d, 3H) ppm; HPLC (Method A) 3.837 min.

Workup

  1. temperaturewas refluxed 1 h
  2. temperaturecooled
  3. filtrationfiltered
  4. washwashing with 1:1 ethyl acetate
  5. customThe filtrate was evaporated
  6. custompurified by flash chromatography (SiO2)
  7. washeluted with 2:98 ethyl acetate

Sources & evidence

ORD record
ord-6cd43b63af764d2a90327ff65ef57174
Source dataset
uspto-grants-2011_03
Patent number
US07902239B2

Reaction notes

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