Sulfuric Acid → 1-Bromo-4-(2-nitroprop-1-en-1-yl)benzene

HRID 1167211Notes

Reaction equation

HRID 1167211 reaction equation
[Br:1][C:2]1[CH:9]=[CH:8][C:5]([CH:6]=O)=[CH:4][CH:3]=1.[N+:10]([CH2:13][CH3:14])([O-:12])=[O:11].C([O-])(=O)C.[NH4+].S(=O)(=O)(O)O>C1(C)C=CC=CC=1>[Br:1][C:2]1[CH:9]=[CH:8][C:5]([CH:6]=[C:13]([N+:10]([O-:12])=[O:11])[CH3:14])=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 1118Sulfuric AcidHCID 6587NitroethaneHCID 707414-BromobenzaldehydeHCID 517165Ammonium Acetate

Product 1

HCID 534140351-Bromo-4-(2-nitroprop-1-en-1-yl)benzeneYield 47.7%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
80 °C

Procedure

A solution of 30.0 g (162 mmol) of 4-bromobenzaldehyde, 116 mL (1.6 mole) of nitroethane, and 37.5 g (486 mmol) of ammonium acetate in 200 mL of toluene was heated under a Dean and Stark trap for 18 hours. The mixture was then cooled to 80° C., 1 mL of concentrated sulfuric acid was added, and the mixture was stirred at 80° C. for 2 hours. The mixture was then cooled to ambient temperature and washed with 200 mL of brine. The organic layer was separated and the aqueous layer was extracted three times with 60 mL of diethyl ether. The combined organics were dried (MgSO4), filtered and concentrated in vacuo. The residue was recrystallized from methanol to afford 18.7 g (47%) of the title compound.

Workup

  1. temperatureThe mixture was then cooled to ambient temperature
  2. washwashed with 200 mL of brine
  3. customThe organic layer was separated
  4. extractionthe aqueous layer was extracted three times with 60 mL of diethyl ether
  5. dry with materialThe combined organics were dried (MgSO4)
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customThe residue was recrystallized from methanol

Sources & evidence

ORD record
ord-0e9d0a29417f42089144cc42d7ca90bf
Source dataset
uspto-grants-2003_09
Patent number
US06617351B1

Reaction notes

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