Hydrogen Bromide → 5-Bromo-2-methylbenzonitrile

HRID 234763Notes

Reaction equation

HRID 234763 reaction equation
N([O-])=O.[Na+].N[C:6]1[CH:7]=[C:8]([C:11]([CH3:14])=[CH:12][CH:13]=1)[C:9]#[N:10].O.[BrH:16]>S(=O)(=O)(O)O.C(O)(=O)C.[Cu]Br>[Br:16][C:6]1[CH:7]=[C:8]([C:11]([CH3:14])=[CH:12][CH:13]=1)[C:9]#[N:10]

Participants

8

Reactant 4

HCID 260Hydrogen BromideHCID 962WaterHCID 27353655-Amino-2-methylbenzonitrileHCID 23668193Sodium Nitrite

Product 1

HCID 129940045-Bromo-2-methylbenzonitrileYield 44.5%

Reagents, catalysts & solvents 3

HCID 24593copper(I) bromideCatalystHCID 176Acetic AcidSolventHCID 1118Sulfuric AcidSolvent

Procedure

15.2 g (0.22 mol) of sodium nitrite are heated to 70° C. in 160 ml of concentrated sulphuric acid and the solution formed is added dropwise to a solution of 26.4 g (0.2 mol) of the compound from Example XV in 400 ml of glacial acetic acid at 20° C. to 40° C. A solution of 63.1 g (0.44 mol) of copper(I) bromide in 400 ml of concentrated hydrobromic acid is added dropwise to this solution at 10° C. to 20° C. and the mixture is stirred for 0.5 hour. The reaction mixture is introduced into 11 of water, the precipitate which has separated out is filtered off with suction, washed with water and suspended in methylene chloride and the insoluble material is filtered off with suction. The filtrate is washed with saturated sodium chloride solution, dried over sodium sulphate and concentrated to give 19.2 g of the title compound.

Workup

  1. customthe solution formed
  2. customthe precipitate which has separated out
  3. filtrationis filtered off with suction
  4. washwashed with water
  5. filtrationthe insoluble material is filtered off with suction
  6. washThe filtrate is washed with saturated sodium chloride solution
  7. dry with materialdried over sodium sulphate
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-f1561e61898748a3a269f986c1bff134
Source dataset
uspto-grants-1997_01
Patent number
US05596006

Reaction notes

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