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

HRID 2209257Notes

Reaction equation

HRID 2209257 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-olYield 30.4%

Reagents, catalysts & solvents 1

HCID 14798Sodium HydroxideSolvent2×

Procedure

A solution of Bromine (8.82 g) in 10% of aqueous sodium hydroxide (53 mL) was added drop-wise to a solution of 5-chloropyridin-3-ol (7.2 g) with stirring in 10% aqueous sodium hydroxide (50 mL). After addition was completed, the mixture was cooled with ice-bath and neutralized with concentrated HCl. The product was precipitated, collected by filtration and washed with water to provide 3.5 g of 2-bromo-5-chloropyridin-3-ol was obtained. LCMS [M+H]+: 209.13.

Workup

  1. additionAfter addition
  2. customThe product was precipitated
  3. filtrationcollected by filtration
  4. washwashed with water

Sources & evidence

ORD record
ord-31bb840894bf4d388e1e1c33e8831f49
Source dataset
uspto-grants-2016_06
Patent number
US09376441B2

Reaction notes

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