Lithium Hydroxide → HCID 71239887, compound

HRID 873106Notes

Reaction equation

HRID 873106 reaction equation
[Br:1][C:2]1[C:3]([O:12][C:13]2[CH:18]=[CH:17][CH:16]=[C:15]([C:19]([F:22])([F:21])[F:20])[CH:14]=2)=[N:4][CH:5]=[C:6]([CH:11]=1)[C:7]([O:9]C)=[O:8].[Li+].[OH-]>CO.O1CCCC1.O>[Br:1][C:2]1[C:3]([O:12][C:13]2[CH:18]=[CH:17][CH:16]=[C:15]([C:19]([F:21])([F:22])[F:20])[CH:14]=2)=[N:4][CH:5]=[C:6]([CH:11]=1)[C:7]([OH:9])=[O:8]

Participants

6

Reactant 2

HCID 3939Lithium HydroxideHCID 71239727HCID 71239727, compound

Product 1

HCID 71239887HCID 71239887, compoundYield 102.3%

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of methyl 5-bromo-6-(3-(trifluoromethyl)phenoxy)nicotinate (610 mg, 1.62 mmol) in methanol (4.00 mL), tetrahydrofuran (THF) (4 mL) and water (2.000 mL) was added LiOH (117 mg, 4.87 mmol) at rt. The reaction mixture was stirred at rt for 3 h, quenched with HCl and concentrated. Purification via ISCO system (ethyl acetate/petroleum ether=1/10) afforded the title product (600 mg).

Workup

  1. customquenched with HCl
  2. concentrationconcentrated
  3. customPurification via ISCO system (ethyl acetate/petroleum ether=1/10)

Sources & evidence

ORD record
ord-816872e6702345bfa4b11bf279a237ba
Source dataset
uspto-grants-2015_03
Patent number
US08975400B2

Reaction notes

Loading…