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

HRID 385914Notes

Reaction equation

[Br:1][C:2]1[N:7]=[C:6]([C:8]([CH3:12])([CH3:11])[C:9]#N)[CH:5]=[CH:4][CH:3]=1.[OH-:13].[Na+].C[OH:16]>C(OCC)(=O)C.O>[Br:1][C:2]1[N:7]=[C:6]([C:8]([CH3:12])([CH3:11])[C:9]([OH:16])=[O:13])[CH:5]=[CH:4][CH:3]=1

Participants

Conditions

Temperature: 80 °C

Procedure

To a solution of 2-(6-bromopyridin-2-yl)-2-methylpropanenitrile (Example 367, Step 1) (50 mg, 0.22 mmol) in methanol (2 mL) was added 1 N aqueous sodium hydroxide (2 mL) and the mixture was heated to 80° C. overnight. The reaction was then 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 2 N hydrochloric acid solution and extracted with ethyl acetate (15 mL). The organic layer was dried over sodium sulfate, filtered and concentrated to yield the title compound.

Workup

temperatureThe reaction was then cooled to ambient temperature
customthe layers were separated
extractionextracted with ethyl acetate (15 mL)
dry with materialThe organic layer was dried over sodium sulfate
filtrationfiltered
concentrationconcentrated

Sources & evidence

ORD record: ord-be9854e9a0e040d7828219353d31c3a7
Source dataset: uspto-grants-2013_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08367706B2

Reaction notes

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