Hydrogen Bromide → 2,5-Dibromo-3-nitropyridine

HRID 2422680Notes

Reaction equation

HRID 2422680 reaction equation
[BrH:1].[Br:2][C:3]1[CH:4]=[C:5]([N+:10]([O-:12])=[O:11])[C:6](N)=[N:7][CH:8]=1.BrBr.S([O-])([O-])=O.[Na+].[Na+].[OH-].[Na+]>>[Br:1][C:6]1[C:5]([N+:10]([O-:12])=[O:11])=[CH:4][C:3]([Br:2])=[CH:8][N:7]=1

Participants

6

Reactant 5

HCID 260Hydrogen BromideHCID 14798Sodium HydroxideHCID 24408BromineHCID 24437Sodium SulfiteHCID 1388782-Amino-5-bromo-3-nitropyridine

Product 1

HCID 2984702,5-Dibromo-3-nitropyridineYield 58.9%

Conditions

Temperature
0 °C

Procedure

Hydrogen bromide (48% in H2O, 13 mL) was stirred at 0° C., to which 5-bromo-3-nitropyridin-2-amine (5.0 g, 22.9 mmol) was dropwise added with its inner temperature kept at 5° C. or lower. After the addition, bromine (4.69 mL) and sodium sulfite (6.32 g) were added to it in that order. After stirred at 0° C. for 45 minutes, aqueous sodium hydroxide (9.16 g) solution (10 mL) was added thereto and stirred at room temperature for 1 hour. The resulting solid was taken out through filtration, washed with water and dried to obtain the intended compound (3.80 g, 58.9%).

Workup

  1. additionwas dropwise added with its inner temperature
  2. customkept at 5° C.
  3. additionwere added to it in that order
  4. stirringstirred at room temperature for 1 hour
  5. filtrationThe resulting solid was taken out through filtration
  6. washwashed with water
  7. customdried

Sources & evidence

ORD record
ord-223b70a91784440eadcb35f4007ec0d5
Source dataset
uspto-grants-2011_06
Patent number
US07960394B2

Reaction notes

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