Methanol → 2-(6-Bromopyridin-2-yl)acetic acid

HRID 385855

Reaction equation

HRID 385855 reaction equation
[Br:1][C:2]1[N:7]=[C:6]([CH2:8][C:9]#N)[CH:5]=[CH:4][CH:3]=1.[OH-:11].[Na+].C[OH:14]>C(OCC)(=O)C.O>[Br:1][C:2]1[N:7]=[C:6]([CH2:8][C:9]([OH:14])=[O:11])[CH:5]=[CH:4][CH:3]=1

Participants

6

Conditions

Temperature
80 °C

Procedure

(6-Bromopyridin-2-yl)acetonitrile (50 mg, 0.25 mmol) was taken up in methanol (2 mL) and 1 N aqueous sodium hydroxide (2 ml, 2 mmol) was added. The reaction was heated to 80° C. overnight. Upon completion, the reaction was cooled to ambient temperature, diluted with ethyl acetate (15 mL) and water (15 mL), and the layers were separated. The aqueous layer was acidified with 2N aqueous hydrochloric acid and extracted with ethyl acetate. The organic layer was dried over magnesium sulfate, filtered, and concentrated in vacuo to afford the title compound which was used without further purification.

Workup

  1. temperatureUpon completion, the reaction was cooled to ambient temperature
  2. customthe layers were separated
  3. extractionextracted with ethyl acetate
  4. dry with materialThe organic layer was dried over magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-aeefa89cac284b3c991110c380b5d1c7
Source dataset
uspto-grants-2013_02
Patent number
US08367706B2

Linked notes

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