Hydrochloric Acid → HCID 90229449, compound

HRID 1505754Notes

Reaction equation

HRID 1505754 reaction equation
[Cl:1][C:2]1[CH:11]=[CH:10][C:9]([O:12][CH2:13][CH:14]([F:16])[F:15])=[CH:8][C:3]=1[C:4]([O:6]C)=[O:5].[OH-].[Li+].Cl>CO>[Cl:1][C:2]1[CH:11]=[CH:10][C:9]([O:12][CH2:13][CH:14]([F:15])[F:16])=[CH:8][C:3]=1[C:4]([OH:6])=[O:5]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 3939Lithium HydroxideHCID 90229320HCID 90229320, compound

Product 1

HCID 90229449HCID 90229449, compoundYield 53.9%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of methyl 2-chloro-5-(2,2-difluoroethoxy)benzoate (55 mg) in MeOH (1 mL) was added 1M aqueous lithium hydroxide (0.88 mL), and the solution was stirred at room temperature for 12 hours. The reaction mixture was stirred under ice-cooling, 2M hydrochloric acid was added slowly to acidify to pH 2-3, and the precipitated solid was filtered. The solid was washed sequentially with a small amount of water and diethyl ether, and dried under reduced pressure to obtain the titled compound (28 mg) as white powder.

Workup

  1. stirringThe reaction mixture was stirred under ice-
  2. temperaturecooling
  3. filtrationthe precipitated solid was filtered
  4. washThe solid was washed sequentially with a small amount of water and diethyl ether
  5. customdried under reduced pressure

Sources & evidence

ORD record
ord-1e3bc9f5b08941cf85cbca8f3529e977
Source dataset
uspto-grants-2015_12
Patent number
US09216968B2

Reaction notes

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