Cesium fluoride → Ethyl 2-(4-amino-2-chloro-5-ethynylphenoxy)-4-fluorobenzoate

HRID 624384Notes

Reaction equation

HRID 624384 reaction equation
[NH2:1][C:2]1[C:20]([C:21]#[C:22][Si](C)(C)C)=[CH:19][C:5]([O:6][C:7]2[CH:17]=[C:16]([F:18])[CH:15]=[CH:14][C:8]=2[C:9]([O:11][CH2:12][CH3:13])=[O:10])=[C:4]([Cl:27])[CH:3]=1.[F-].[Cs+]>CO>[NH2:1][C:2]1[C:20]([C:21]#[CH:22])=[CH:19][C:5]([O:6][C:7]2[CH:17]=[C:16]([F:18])[CH:15]=[CH:14][C:8]=2[C:9]([O:11][CH2:12][CH3:13])=[O:10])=[C:4]([Cl:27])[CH:3]=1

Participants

4

Reactant 2

HCID 25953Cesium fluorideHCID 67226491Ethyl 2-(4-amino-2-chloro-5-((trimethylsilyl)ethynyl)phenoxy)-4-fluorobenzoate

Product 1

HCID 87316240Ethyl 2-(4-amino-2-chloro-5-ethynylphenoxy)-4-fluorobenzoate

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of EXAMPLE 242C (2.69 g) in methanol (20 mL) was added CsF (5 g). The mixture was stirred at room temperature overnight. The solvent was evaporated and the residue was dissolved in ethyl acetate (200 mL) and washed with water, brine and dried over Na2SO4. The mixture was filtered, and the solvent was evaporated.

Workup

  1. customThe solvent was evaporated
  2. dissolutionthe residue was dissolved in ethyl acetate (200 mL)
  3. washwashed with water, brine
  4. dry with materialdried over Na2SO4
  5. filtrationThe mixture was filtered
  6. customthe solvent was evaporated

Sources & evidence

ORD record
ord-a4755fd3f0134e55aec8878469d10041
Source dataset
uspto-grants-2016_04
Patent number
US09303025B2

Reaction notes

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