Hydrogen Bromide → HCID 69741683, compound

HRID 495680Notes

Reaction equation

HRID 495680 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:7]=[C:8]([O:10][CH3:11])[CH:9]=1)N.N([O-])=O.[Na+].[BrH:16]>[Cu]Br>[Br:16][C:8]1([O:10][CH3:11])[CH:7]=[CH:5][CH:4]=[C:3]([O:2][CH3:1])[CH2:9]1

Participants

5

Reactant 3

HCID 260Hydrogen Bromide2×HCID 663013,5-DimethoxyanilineHCID 23668193Sodium Nitrite

Product 1

HCID 69741683HCID 69741683, compoundYield 40%

Reagents, catalysts & solvents 1

HCID 24593copper(I) bromideCatalyst

Procedure

100 mmol of 3,5-dimethoxyaniline were mixed with 75 ml of 48% hydrobromic acid. 150 mmol of sodium nitrite powder were added portionally over 20 minutes with rigorous stirring. The reaction was monitored by iodine-starch test paper until the paper turned blue. The resulting diazonium salt solution was added to a pre-prepared boiling solution of 50 mmol copper (I) bromide in 7 ml of 48% hydrobromic acid. The addition was complete after 20 minutes. The reaction mixture was then heated for 30 minutes with rigorous stirring. Steam distillation of the reaction mixture provided a white solid product with a yield of 40%.

Workup

  1. additionThe addition
  2. temperatureThe reaction mixture was then heated for 30 minutes with rigorous stirring
  3. distillationSteam distillation of the reaction mixture
  4. customprovided a white solid product with a yield of 40%

Sources & evidence

ORD record
ord-5caa6be6f11940ed83a4df74769f4b7f
Source dataset
uspto-grants-2005_09
Patent number
US06939977B2

Reaction notes

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