Methanol → Methyl 5-bromo-6-(isobutylthio)picolinate
Reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][C:5]([C:13]([OH:15])=[O:14])=[N:6][C:7]=1[S:8][CH2:9][CH:10]([CH3:12])[CH3:11].S(=O)(=O)(O)O.[CH3:21]O>>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([C:13]([O:15][CH3:21])=[O:14])=[N:6][C:7]=1[S:8][CH2:9][CH:10]([CH3:12])[CH3:11]Participants
4
Conditions
- Temperature
- 80 °C
Procedure
5-Bromo-6-(isobutylthio)picolinic acid (500 mg, 1.72 mmol) was dissolved in methanol (5 mL) to give a yellow solution. Sulfuric acid (169 mg, 92.3 μL, 1.72 mmol) was added. The reaction mixture was heated to 80° C. and stirred for 1 d. The reaction mixture was cooled to 0° C. and poured onto ice-water/brine (25 mL). The aqueous layer was extracted with EtOAc (2×40 mL) and washed with ice-water/brine (20 mL). The organic layers were combined, dried over Na2SO4 and concentrated in vacuo to give crude title compound as a yellow oil. The oil was purified by flash chromatography (silica gel, 5 g, 0% to 15% EtOAc in heptane) to give the title product (205 mg, 39%) as a colorless oil. MS (EI): m/e=306.3 [M+H]+.
Workup
- customto give a yellow solution
- temperatureThe reaction mixture was cooled to 0° C.
- additionpoured onto ice-water/brine (25 mL)
- extractionThe aqueous layer was extracted with EtOAc (2×40 mL)
- washwashed with ice-water/brine (20 mL)
- dry with materialdried over Na2SO4
- concentrationconcentrated in vacuo
- customto give crude title compound as a yellow oil
- customThe oil was purified by flash chromatography (silica gel, 5 g, 0% to 15% EtOAc in heptane)
Sources & evidence
- ORD record
- ord-fbce10cae94342bd8399490c5d7be23b
- Source dataset
- uspto-grants-2016_04
- Patent number
- US09303012B2
Reaction notes
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