Lithium Hydroxide → HCID 67461925, compound

HRID 2171116Notes

Reaction equation

HRID 2171116 reaction equation
[Br:1][C:2]1[C:7]([O:8][CH2:9][C:10]([O:12]CC)=[O:11])=[C:6]([O:15][CH3:16])[C:5]([O:17][CH:18]([F:20])[F:19])=[CH:4][CH:3]=1.[OH-].[Li+]>O1CCCC1.O>[Br:1][C:2]1[C:7]([O:8][CH2:9][C:10]([OH:12])=[O:11])=[C:6]([O:15][CH3:16])[C:5]([O:17][CH:18]([F:19])[F:20])=[CH:4][CH:3]=1

Participants

5

Reactant 2

HCID 3939Lithium HydroxideHCID 67465860HCID 67465860, compound

Product 1

HCID 67461925HCID 67461925, compoundYield 66%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a stirring solution of ethyl 2-(6-bromo-3-(difluoromethoxy)-2-methoxyphenoxy)acetate (300 mg, 0.845 mmol) in tetrahydrofuran was added lithium hydroxide in water and the reaction mixture was stirred at RT for 1 h. The reaction mixture was concentrated under reduced pressure and the obtained residue was acidified to pH 2 and then extracted with ethyl acetate. The combined ethyl acetate layers were dried over sodium sulphate and concentrated under reduced pressure to afford 2-(6-Bromo-3-(difluoromethoxy)-2-methoxyphenoxy)acetic acid as a solid (180 mg, 66%).

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. extractionextracted with ethyl acetate
  3. dry with materialThe combined ethyl acetate layers were dried over sodium sulphate
  4. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-fb4cebdfe8fe48c4b77597b44f86edc3
Source dataset
uspto-grants-2015_06
Patent number
US09051290B2

Reaction notes

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