Hydrochloric Acid → 1-(5-Bromopyridin-2-yl)cyclopropane-1-carboxylic acid
Reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2([C:11]#N)[CH2:10][CH2:9]2)=[N:6][CH:7]=1.[OH-:13].[Na+].Cl.C([OH:18])C>>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2([C:11]([OH:18])=[O:13])[CH2:10][CH2:9]2)=[N:6][CH:7]=1Participants
Procedure
A flask charged with a stir bar, 1-(5-bromo-pyridin-2-yl)-cyclopropanecarbonitrile (1.00 g), 25% aqueous NaOH solution (1 mL), and ethanol (10 mL) was heated to 100° C., and the mixture was stirred at this temperature for 14 h. After cooling to room temperature, the solution was poured into ice-cold saturated aqueous Na2HPO4 solution and the resulting mixture was adjusted to pH 4 by the addition of 1 M aqueous hydrochloric acid. The mixture was extracted with ethyl acetate and the combined extracts were washed with brine and dried (MgSO4). The solvent was evaporated and the residue was recrystallized from diisopropyl ether to give the title compound as a yellowish solid. Yield: 0.58 g (53% of theory); LC (method 1): tR=0.60 min; Mass spectrum (ESI+): m/z=242/244 (Br) [M+H]+.
Workup
- additionA flask charged with a stir bar
- additionthe solution was poured into ice-cold saturated aqueous Na2HPO4 solution
- extractionThe mixture was extracted with ethyl acetate
- washthe combined extracts were washed with brine
- dry with materialdried (MgSO4)
- customThe solvent was evaporated
- customthe residue was recrystallized from diisopropyl ether
Sources & evidence
- ORD record
- ord-cc0602c1598c46f89f5e68de6df60524
- Source dataset
- uspto-grants-2015_07
- Patent number
- US09090605B2
Reaction notes
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