Water → 5-Bromo-2-methoxypyridine

HRID 454805Notes

Reaction equation

HRID 454805 reaction equation
[CH3:1][OH:2].C[O-].[Na+].[Br:6][C:7]1[CH:8]=[CH:9][C:10](Cl)=[N:11][CH:12]=1.O>CO>[CH3:1][O:2][C:10]1[CH:9]=[CH:8][C:7]([Br:6])=[CH:12][N:11]=1

Participants

5

Reactant 3

HCID 962WaterHCID 27344145-Bromo-2-chloropyridineHCID 23694274Sodium methanolate methanol

Product 1

HCID 27348955-Bromo-2-methoxypyridineYield 33%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
90 °C

Procedure

A 0.5 M sodium methoxide methanol solution (NaOMe in MeOH, 10.4 mL, 5.19 mmol) was added to 5-bromo-2-chloropyridine (96, 500 mg, 2.59 mmol) dissolved in methanol (10 mL) at room temperature, stirred at 90° C. for 24 hours, followed by adding water. Organic compounds were extracted with ethyl acetate and evaporated after a treatment with sodium sulfate. Purification was performed by column chromatograph to give the target compound 2-methoxy-5-bromopyridine (97a, 160 mg, 33%).

Workup

  1. extractionOrganic compounds were extracted with ethyl acetate
  2. customevaporated after a treatment with sodium sulfate
  3. customPurification

Sources & evidence

ORD record
ord-400f3131852041d3919fdc6c7632c36c
Source dataset
uspto-grants-2013_07
Patent number
US08497260B2

Reaction notes

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