Acetic Acid → Benzonitrile, 3-bromo-4-hydroxy-5-nitro-

HRID 2090082Notes

Reaction equation

HRID 2090082 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([CH:7]=[C:8](Br)[C:9]=1[OH:10])[C:5]#[N:6].C(O)(=O)C.[N:16]([O-:18])=[O:17].[Na+].O>C(OCC)(=O)C>[Br:1][C:2]1[CH:3]=[C:4]([CH:7]=[C:8]([N+:16]([O-:18])=[O:17])[C:9]=1[OH:10])[C:5]#[N:6]

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 962WaterHCID 15531BromoxynilHCID 23668193Sodium Nitrite

Product 1

HCID 3014048Benzonitrile, 3-bromo-4-hydroxy-5-nitro-Yield 116.2%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
50 °C

Procedure

To a 5-L, 3-neck round-bottom flask fitted with a thermocouple, stirring paddle, and nitrogen line were added 3,5-dibromo-4-hydroxybenzonitrile (95 g) and glacial acetic acid (3.3 L). Sodium nitrite (120 g) was then added in small portions. The mixture was heated to 50° C. and stirred overnight at this temperature. The mixture was then allowed to cool and poured into a large extractor containing water (10 L). Ethyl acetate (10 L) was added and the layers were separated. The aqueous layer was extracted with ethyl acetate (4 L) and the combined organic layers were washed with water and brine, and then dried over magnesium sulfate and concentrated in vacuo to provide 96.9 g of the desired product. Mass spectrum (ESI) 243.0 (M+).

Workup

  1. stirringstirred overnight at this temperature
  2. temperatureto cool
  3. additionpoured into a large extractor
  4. customthe layers were separated
  5. extractionThe aqueous layer was extracted with ethyl acetate (4 L)
  6. washthe combined organic layers were washed with water and brine
  7. dry with materialdried over magnesium sulfate
  8. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-5ae6ebe2edf1447c92ac869e4dc9305e
Source dataset
uspto-grants-2013_05
Patent number
US08436028B2

Reaction notes

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