Hydrogen Bromide → HCID 67259836, compound

HRID 536625Notes

Reaction equation

HRID 536625 reaction equation
[CH3:1][C:2]1[N:3]([C:7]2[CH:13]=[CH:12][C:10](N)=[CH:9][CH:8]=2)[CH:4]=[CH:5][N:6]=1.N([O-])=O.[Na+].[BrH:18]>O>[Br:18][C:10]1[CH:12]=[CH:13][C:7]([N:3]2[CH:4]=[CH:5][N:6]=[C:2]2[CH3:1])=[CH:8][CH:9]=1

Participants

5

Reactant 3

HCID 260Hydrogen Bromide2×HCID 31574784-(2-methyl-1H-imidazol-1-yl)anilineHCID 23668193Sodium Nitrite

Product 1

HCID 67259836HCID 67259836, compoundYield 51%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

To a solution of 4-(2-methyl-1H-imidazol-1-yl)aniline (10 g, 57.8 mmol) in 100 mL of HBr solution was added a solution of NaNO2 (5.2 g, 75.1 mmol) in H2O (60 mL) at 0° C. Stirred at this temperature for 20 min., then poured the mixture into a solution of CuBr (58 g, 404 mmol) in HBr solution (200 mL) at 0° C., and stirred for 30 min., diluted with water, and stirred at room temperature for 1 hour. The precipitate was separated out, and evaporated in vacuo to give 28 g of crude product, which was purified by Prep-HPLC to obtain 1-(4-bromophenyl)-2-methyl-1H-imidazole (7 g, yield 51%).

Workup

  1. stirringstirred for 30 min.
  2. stirringstirred at room temperature for 1 hour
  3. customThe precipitate was separated out
  4. customevaporated in vacuo
  5. customto give 28 g of crude product, which
  6. customwas purified by Prep-HPLC

Sources & evidence

ORD record
ord-ae35aca0aae84f45a862e1e3eace1053
Source dataset
uspto-grants-2014_10
Patent number
US08859611B2

Reaction notes

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