Sodium Hydroxide → 5-Bromo-6-chloropyridin-3-ol
Reaction equation
C([O:4][C:5]1[CH:6]=[N:7][C:8]([Cl:12])=[C:9]([Br:11])[CH:10]=1)(=O)C.[OH-].[Na+]>C1COCC1>[Br:11][C:9]1[CH:10]=[C:5]([OH:4])[CH:6]=[N:7][C:8]=1[Cl:12]Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 0 °C
Procedure
To a stirred mixture of 5-bromo-6-chloropyridin-3-yl acetate (3.98 g, 15.89 mmol) in THF (20 mL) at 0° C. was added sodium hydroxide (20 mL, 50.0 mmol, 2.5 M in water). The reaction mixture was stirred at 0° C. for 45 min. The reaction mixture was partially concentrated and then taken to a pH of around 7 by adding acetic acid. The resulting precipitate was filtered and washed with water to give 5-bromo-6-chloropyridin-3-ol. MS (ESI, pos. ion) m/z: 207.9 and 209.9 (M+1).
Workup
- concentrationThe reaction mixture was partially concentrated
- additionby adding acetic acid
- filtrationThe resulting precipitate was filtered
- washwashed with water
Sources & evidence
- ORD record
- ord-db5a3eddf9da4603b19d1f27dec24626
- Source dataset
- uspto-grants-2014_01
- Patent number
- US08637500B2
Reaction notes
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