Hydrochloric Acid → 5-Bromo-6-(isobutylthio)picolinic acid

HRID 927811Notes

Reaction equation

[Br:1][C:2]1[CH:3]=[CH:4][C:5]([C:9]([OH:11])=[O:10])=[N:6][C:7]=1Cl.[CH3:12][CH:13]([CH3:16])[CH2:14][SH:15].C(=O)([O-])[O-].[Cs+].[Cs+].Cl>CS(C)=O>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([C:9]([OH:11])=[O:10])=[N:6][C:7]=1[S:15][CH2:14][CH:13]([CH3:16])[CH3:12]

Participants

Conditions

Temperature: 150 °C

Procedure

5-Bromo-6-chloropicolinic acid (2 g, 8.46 mmol; CAN 959958-25-9), 2-methylpropane-1-thiol (915 mg, 1.1 mL, 10.2 mmol) and cesium carbonate (6.89 g, 21.1 mmol) were suspended in DMSO (100 mL). The reaction mixture was heated to 150° C. and stirred for 1 d and was poured onto icewater/1N HCl (100 mL). The aqueous layer was extracted with EtOAc (2×250 mL). The combined extracts were washed with icewater/brine (100 mL), dried over Na2SO4 and concentrated in vacuo to give the title compound (2.49 g, 51%) as an orange solid which was used in the next step without further purification. MS (EI): m/e=288.4 [M−H]−.

Workup

extractionThe aqueous layer was extracted with EtOAc (2×250 mL)
washThe combined extracts were washed with icewater/brine (100 mL)
dry with materialdried over Na2SO4
concentrationconcentrated in vacuo

Sources & evidence

ORD record: ord-2cb36e03dcd34f38b76c8802ffb40348
Source dataset: uspto-grants-2016_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09290451B2

Reaction notes

Loading…