Reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][C:5]([C:9]([OH:11])=[O:10])=[N:6][C:7]=1Cl.[OH-].[K+].[O:14]1[CH2:18][CH2:17][CH2:16][CH:15]1[CH2:19][OH:20].[OH-].[Na+]>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[O:20][CH2:19][CH:15]1[CH2:16][CH2:17][CH2:18][O:14]1Participants
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Procedure
5-Bromo-6-chloropicolinic acid (200 mg, 846 μmol; CAN 959958-25-9) and powdered potassium hydroxide (190 mg, 3.38 mmol) were combined with DMSO (1.93 mL) to give a colorless solution which was stirred for 15 min at ambient temperature before tetrahydro-2-furanmethanol (130 mg, 123 μl, 1.27 mmol, CAN 97-99-4) was added, and stirring continued for 1 day at ambient temperature. The reaction mixture was poured into a mixture of ice-water and 1 M NaOH, and extracted with t-butylmethyl ether (2×25 mL) and washed with ice-water/brine. The water phases were combined acidified with ice/1 N HCl and extracted with isopropyl acetate (2×30 mL). The organic layers were washed with ice-water/brine (2×30 mL), dried with Na2SO4 and concentrated in vacuo to give the title compound (254 mg, 99%) as light brown oil; MS (ESI): 301.8 [M−H]−.
Workup
- customto give a colorless solution which
- additionwas added
- extractionextracted with t-butylmethyl ether (2×25 mL)
- washwashed with ice-water/brine
- extractionextracted with isopropyl acetate (2×30 mL)
- washThe organic layers were washed with ice-water/brine (2×30 mL)
- dry with materialdried with Na2SO4
- concentrationconcentrated in vacuo
Sources & evidence
- ORD record
- ord-0e6956b8de674381bb2083f49f3d37ed
- Source dataset
- uspto-grants-2016_04
- Patent number
- US09321727B2
Linked notes
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