Lithium Hydroxide → HCID 22312220, compound

HRID 965700Notes

Reaction equation

HRID 965700 reaction equation
[N:1]([CH:4]([C:9]1[CH:14]=[C:13]([F:15])[CH:12]=[C:11]([F:16])[CH:10]=1)[C:5]([O:7]C)=[O:6])=[N+:2]=[N-:3].[OH-].[Li+]>C1COCC1>[N:1]([CH:4]([C:9]1[CH:10]=[C:11]([F:16])[CH:12]=[C:13]([F:15])[CH:14]=1)[C:5]([OH:7])=[O:6])=[N+:2]=[N-:3]

Participants

4

Reactant 2

HCID 3939Lithium HydroxideHCID 22312564HCID 22312564, compound

Product 1

HCID 22312220HCID 22312220, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of methyl 2-azido-2-(3,5-difluorophenyl)acetate in THF/H20 (2.6:1) cooled to 0° C. was added 1.7 eq. of lithium hydroxide. The reaction mixture was stirred at room temperature for 3 hours and then poured into a separatory funnel. The mixture was extracted into water and washed with ether. The aqueous layer was acidified with 1N HCl and extracted with ethyl acetate. The organic layer was then washed with water and brine. The organic layer was dried over sodium sulfate, filtered and concentrated under reduced pressure to give 2-azido-2-(3,5-difluorophenyl)acetic acid.

Workup

  1. additionpoured into a separatory funnel
  2. extractionThe mixture was extracted into water
  3. washwashed with ether
  4. extractionextracted with ethyl acetate
  5. washThe organic layer was then washed with water and brine
  6. dry with materialThe organic layer was dried over sodium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-fe4483e088af460b8cbefc5370b9d77b
Source dataset
uspto-grants-2005_10
Patent number
US06951854B1

Reaction notes

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