Hydrochloric Acid → 2-Bromo-5-chloropyridin-3-ol

HRID 1031493Notes

Reaction equation

HRID 1031493 reaction equation
[Br:1]Br.[Cl:3][C:4]1[CH:5]=[C:6]([OH:10])[CH:7]=[N:8][CH:9]=1.Cl>[OH-].[Na+]>[Br:1][C:7]1[C:6]([OH:10])=[CH:5][C:4]([Cl:3])=[CH:9][N:8]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 24408BromineHCID 5823053-Hydroxy-5-chloropyridine

Product 1

HCID 147400532-Bromo-5-chloropyridin-3-ol

Reagents, catalysts & solvents 1

HCID 14798Sodium HydroxideSolvent2×

Conditions

Temperature
22 °C

Procedure

A solution of bromine (12.35 g) in 10% NaOH (70 mL) was added dropwise with stirring to a solution of 5-chloro-3-pyridinol (10.00 g) in 10% NaOH (70 mL). After the addition was complete, the reaction was stirred at 22° C. for 20 h. The reaction was cooled to 0° C. and acidified to pH 5.3 with concentrated HCl (aq). The precipitate was filtered and dried under vacuum for 60 h to afford a) (15.66 g, 97%).

Workup

  1. additionAfter the addition
  2. temperatureThe reaction was cooled to 0° C.
  3. filtrationThe precipitate was filtered
  4. customdried under vacuum for 60 h
  5. customto afford a) (15.66 g, 97%)

Sources & evidence

ORD record
ord-acdac9a1d85a427d9dd271083758cb09
Source dataset
uspto-grants-1990_09
Patent number
US04954502

Reaction notes

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