Nitric Acid → 1-(3-Bromopropyl)-4-nitrobenzene

HRID 862818Notes

Reaction equation

HRID 862818 reaction equation
S(=O)(=O)(O)O.[N+:6]([O-:9])(O)=[O:7].[C:10]1([CH2:16][CH2:17][CH2:18][Br:19])[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1>>[N+:6]([C:13]1[CH:14]=[CH:15][C:10]([CH2:16][CH2:17][CH2:18][Br:19])=[CH:11][CH:12]=1)([O-:9])=[O:7]

Participants

4

Reactant 3

HCID 944Nitric AcidHCID 1118Sulfuric AcidHCID 12503(3-Bromopropyl)benzene

Product 1

HCID 104444821-(3-Bromopropyl)-4-nitrobenzeneYield 36.7%

Procedure

Concentrated sulfuric acid (18.3 g) was gradually added dropwise to 13.94 g of concentrated nitric acid and the mixture was vigorously shaken for 10 minutes. To the mixed solution, 10 g of 3-phenylpropyl bromide was gradually added dropwise at -20° C. and the mixture was stirred at -20° C. for 1 hour. The reaction mixture was poured into 500 ml of ice water and extracted with ether. The extract was washed and dried, and the solvent was distilled away. The residue was purified by silica gel column chromatography (ethyl acetate:hexane=1:9) to give 4.5 g of 3-(4-nitrophenyl)propyl bromide as a colorless, oily substance.

Workup

  1. stirringthe mixture was stirred at -20° C. for 1 hour
  2. extractionextracted with ether
  3. washThe extract was washed
  4. customdried
  5. distillationthe solvent was distilled away
  6. customThe residue was purified by silica gel column chromatography (ethyl acetate:hexane=1:9)

Sources & evidence

ORD record
ord-f2453804c00d4418af84ee14187c2254
Source dataset
uspto-grants-1998_02
Patent number
US05719176

Reaction notes

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