Butylamine → 2-bromo-1-cyclohexyloxy-4-((E)-2-nitro-hex-1-enyl)-benzene

HRID 402001Notes

Reaction equation

HRID 402001 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][C:9]=1[O:10][CH:11]1[CH2:16][CH2:15][CH2:14][CH2:13][CH2:12]1)[CH:5]=O.[N+:17]([CH2:20][CH2:21][CH2:22][CH2:23][CH3:24])([O-:19])=[O:18].C(N)CCC>C1(C)C=CC=CC=1>[Br:1][C:2]1[CH:3]=[C:4](/[CH:5]=[C:20](/[N+:17]([O-:19])=[O:18])\[CH2:21][CH2:22][CH2:23][CH3:24])[CH:7]=[CH:8][C:9]=1[O:10][CH:11]1[CH2:16][CH2:15][CH2:14][CH2:13][CH2:12]1

Participants

5

Reactant 3

HCID 8007ButylamineHCID 2206391-NitropentaneHCID 630526393-Bromo-4-cyclohexyloxy-benzaldehyde

Product 1

HCID 673721002-bromo-1-cyclohexyloxy-4-((E)-2-nitro-hex-1-enyl)-benzeneYield 70.4%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

3-bromo-4-cyclohexyloxy-benzaldehyde (13 mmol, 3.7 g), 1-nitro-pentane (19.6 mmol, 2.3 g) and n-butyl amine (2.6 mmol, 0.19 g) were dissolved in toluene (5 mL) and refluxed for 48 h. The reaction mixture was cooled, filtered and evaporated the solvent and purified by column chromatography using 2% ethyl acetate in hexane as an eluents to provide 2-bromo-1-cyclohexyloxy-4-((E)-2-nitro-hex-1-enyl)-benzene (3.5 g).

Workup

  1. temperaturerefluxed for 48 h
  2. temperatureThe reaction mixture was cooled
  3. filtrationfiltered
  4. customevaporated the solvent
  5. custompurified by column chromatography

Sources & evidence

ORD record
ord-4796f6d0863f46bba004cd585a488ad3
Source dataset
uspto-grants-2014_06
Patent number
US08741900B2

Reaction notes

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