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

HRID 1972007Notes

Reaction equation

HRID 1972007 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-2624805e55a24b42b07782707b34a535
Source dataset
uspto-grants-2013_04
Patent number
US08431575B2

Reaction notes

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