Potassium Carbonate → 2-(6-Bromopyridin-2-yl)acetic acid
Reaction equation
C([O:3][C:4](=[O:18])[CH:5]([C:11]1[CH:16]=[CH:15][CH:14]=[C:13]([Br:17])[N:12]=1)C(OCC)=O)C.C(=O)([O-])[O-].[K+].[K+].[Cl-].[NH4+]>O>[Br:17][C:13]1[N:12]=[C:11]([CH2:5][C:4]([OH:18])=[O:3])[CH:16]=[CH:15][CH:14]=1Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 100 °C
Procedure
2-(6-Bromo-pyridin-2-yl)-malonic acid diethyl ester (64.0 g, 202.4 mmol) was added to a solution of potassium carbonate (279.8 g, 2024 mmol) in water (400 ml) at rt and the reaction mixture was heated to reflux at 100° C. for 36 h. The reaction mixture was treated with sat. ammonium chloride solution and the product formed was extracted with ethyl acetate (3×800 ml), washed with brine (10 ml). Organic layer was concentrated under reduced pressure to obtain title compound as a pale brown solid. Yield=34.0 g (77.7%). TLC (50% ethyl acetate in hexane) Rf=0.11; LCMS: RtH8=0.45; [M+1]=216.0 and 218.0.
Workup
- temperaturethe reaction mixture was heated
- customthe product formed
- extractionwas extracted with ethyl acetate (3×800 ml)
- washwashed with brine (10 ml)
- concentrationOrganic layer was concentrated under reduced pressure
Sources & evidence
- ORD record
- ord-efe5c67e77bc44a28f6174f4a9de5125
- Source dataset
- uspto-grants-2014_10
- Patent number
- US08865712B2
Reaction notes
Loading…