Bromine → HCID 178517593, compound

HRID 1780059Notes

Reaction equation

HRID 1780059 reaction equation
[Br:1]Br.[Cl:3][C:4]1[C:5]([OH:10])=[N:6][CH:7]=[CH:8][CH:9]=1.S([O-])([O-])=O.[Na+].[Na+]>CN(C)C=O.O>[Br:1][C:8]1[CH:9]=[C:4]([Cl:3])[C:5]([OH:10])=[N:6][CH:7]=1

Participants

6

Reactant 3

HCID 24408BromineHCID 24437Sodium SulfiteHCID 178517711HCID 178517711, compound

Product 1

HCID 178517593HCID 178517593, compoundYield 95.1%

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 6228DimethylformamideSolvent

Procedure

10.5 ml (203.0 mmol) of bromine are added dropwise at 0° C. to 23.9 g (184.5 mmol) of 3-chloro-2-hydroxypyridine in 240 ml of dimethylformamide, and the mixture is stirred at room temperature for 2 hours. 200 ml of water are subsequently added, and 30 g of sodium sulfite in 100 ml of water are added dropwise. After 15 minutes, the mixture is extracted three times with 200 ml of dichloromethane in each case, the combined organic phases are dried over sodium sulfate and filtered, and the filtrate is evaporated to dryness, giving 36.58 g of 5-bromo-3-chloro-2-hydroxypyridine. ##STR13## m.p.: 168° C. (decomp.)

Workup

  1. waitAfter 15 minutes
  2. extractionthe mixture is extracted three times with 200 ml of dichloromethane in each case
  3. dry with materialthe combined organic phases are dried over sodium sulfate
  4. filtrationfiltered
  5. customthe filtrate is evaporated to dryness

Sources & evidence

ORD record
ord-9611d4d8b1064c04a5fd03b49f022668
Source dataset
uspto-grants-1997_05
Patent number
US05629428

Reaction notes

Loading…