Tetrahydrofuran → 5-Bromopyridine-2-carboxylic acid

HRID 557881Notes

Reaction equation

HRID 557881 reaction equation
O.[OH-].[Li+].C[O:5][C:6]([C:8]1[CH:13]=[CH:12][C:11]([Br:14])=[CH:10][N:9]=1)=[O:7].O1CCCC1>O>[Br:14][C:11]1[CH:12]=[CH:13][C:8]([C:6]([OH:7])=[O:5])=[N:9][CH:10]=1

Participants

5

Reactant 3

HCID 8028TetrahydrofuranHCID 168937Lithium hydroxide, monohydrateHCID 7016458Methyl 5-bromopyridine-2-carboxylate

Product 1

HCID 6085445-Bromopyridine-2-carboxylic acid

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Lithium hydroxide, monohydrate (0.39 g, 0.0092 mol) was added to a mixture of 5-bromopyridine-2-carboxylic acid methyl ester (0.25 g, 0.0012 mol) in tetrahydrofuran (4.8 mL, 0.059 mol) and water (2.0 mL) and the reaction mixture was refluxed for 30 minutes. The reaction mixture was concentrated and was adjusted to be acidic (pH=˜4) by adding 1 N HCl. The product was extracted with ethyl acetate and the combined extract was concentrated to give the desired product. LC-MS: 202.0/204.0 (M+H+)

Workup

  1. temperaturethe reaction mixture was refluxed for 30 minutes
  2. concentrationThe reaction mixture was concentrated
  3. additionby adding 1 N HCl
  4. extractionThe product was extracted with ethyl acetate
  5. extractionthe combined extract
  6. concentrationwas concentrated

Sources & evidence

ORD record
ord-b2e23ad4e584495495e0a2f9ac70b18c
Source dataset
uspto-grants-2011_11
Patent number
US08058288B2

Reaction notes

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