Water → Benzonitrile, 3-bromo-4-hydroxy-5-nitro-

HRID 921604

Reaction equation

HRID 921604 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].[N:12]([O-:14])=[O:13].[Na+].BrBr.O>C(O)(=O)C.CO>[Br:1][C:2]1[CH:3]=[C:4]([CH:7]=[C:8]([N+:12]([O-:14])=[O:13])[C:9]=1[OH:10])[C:5]#[N:6]

Participants

7

Reactant 4

HCID 962WaterHCID 15531BromoxynilHCID 24408BromineHCID 23668193Sodium Nitrite

Product 1

HCID 3014048Benzonitrile, 3-bromo-4-hydroxy-5-nitro-Yield 84.2%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 887MethanolSolvent

Conditions

Temperature
50 °C

Procedure

(I1B): To a suspension of 3,5-dibromo-4-hydroxybenzonitrile (2.11 g, 7.62 mmol) in acetic acid (70 mL) was added sodium nitrite (2.63 g, 38.1 mmol) in small portion, evolving bubbles and bromine were observed. After addition, the mixture was stirred at 50° C. overnight. Reaction was cooled to room temperature; water (250 ml) was added and extracted with EtOAc for two times. The combined extracts were washed with water and brine, dried over MgSO4 filtered and the filtrate was concentrated to give yellow orange solid. The solid was treated with small amount of MeOH, collected by filtration, rinsed with MeOH, dried to afford 1.56 g of 3-bromo-4-hydroxy-5-nitrobenzonitrile as yellow solid.

Workup

  1. additionAfter addition
  2. customReaction
  3. temperaturewas cooled to room temperature
  4. extractionextracted with EtOAc for two times
  5. washThe combined extracts were washed with water and brine
  6. dry with materialdried over MgSO4
  7. filtrationfiltered
  8. concentrationthe filtrate was concentrated
  9. customto give yellow orange solid
  10. filtrationcollected by filtration
  11. washrinsed with MeOH
  12. customdried

Sources & evidence

ORD record
ord-5e4a41f8365944babdc5abdc1a0e4049
Source dataset
uspto-grants-2016_03
Patent number
US09273057B2

Linked notes

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