Bromine → HCID 178526832, compound

HRID 2054164Notes

Reaction equation

HRID 2054164 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[CH:4][N:3]=1.[Br:11]Br>O>[Br:11][C:7]1[C:2]([OH:1])=[N:3][CH:4]=[C:5]([N+:8]([O-:10])=[O:9])[CH:6]=1

Participants

4

Reactant 2

HCID 24408BromineHCID 178526703HCID 178526703, compound

Product 1

HCID 178526832HCID 178526832, compoundYield 90%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
40 °C

Procedure

A mixture of 2-hydroxy-5-nitropyridine (50.0 g, 0.358 mol) and water (7 L) was warmed to 40° C. and bromine (21.1 mL, 0.393 mol) was added dropwise over ˜20 min. After stirring at 40° C. for 2.5 h, the mixture was cooled to 10° C. and the crude product was isolated by filtration. The solid was washed with water and dried in vacuo to give 3-bromo-2-hydroxy-5-nitropyridine as a solid (70.0 g, 90% yield). mp 212-214° C. (with decomposition); 1H NMR (CD3OD) δ 8.66 (d, J=2.9 Hz, 1H), 8.64 (d, J=2.9 Hz, 1H).

Workup

  1. temperaturethe mixture was cooled to 10° C.
  2. customthe crude product was isolated by filtration
  3. washThe solid was washed with water
  4. customdried in vacuo

Sources & evidence

ORD record
ord-373b7bc8ce3b49cb87f53de28a47d0e3
Source dataset
uspto-grants-2008_02
Patent number
US07329656B2

Reaction notes

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