Acetic Acid → trans-4-Bromo-beta-nitrostyrene

HRID 1691347Notes

Reaction equation

HRID 1691347 reaction equation
[Br:1][C:2]1[CH:9]=[CH:8][C:5]([CH:6]=O)=[CH:4][CH:3]=1.[N+:10]([CH3:13])([O-:12])=[O:11].C([O-])(=O)C.[NH4+].C(O)(=O)C>O>[Br:1][C:2]1[CH:9]=[CH:8][C:5](/[CH:6]=[CH:13]/[N+:10]([O-:12])=[O:11])=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 6375NitromethaneHCID 707414-BromobenzaldehydeHCID 517165Ammonium Acetate

Product 1

HCID 688204trans-4-Bromo-beta-nitrostyreneYield 83.8%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of 4-bromobenzaldehyde (16.8 g, 91 mmol), nitromethane (24.6 mL, 455 mmol), ammonium acetate (14 g, 182 mmol), and acetic acid (160 mL) was stirred for 4 hours at 100° C. This mixture was cooled to room temperature and poured into water. The precipitate thus produced was collected, washed with water, and dried under a reduced pressure to obtain the title compound (17.4 g). The title compound was used in the following reaction without any further purification.

Workup

  1. temperatureThis mixture was cooled to room temperature
  2. customThe precipitate thus produced
  3. customwas collected
  4. washwashed with water
  5. customdried under a reduced pressure

Sources & evidence

ORD record
ord-4950716c1c2245179dc7d1c6af13daa9
Source dataset
uspto-grants-2012_04
Patent number
US08153662B2

Reaction notes

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