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

HRID 1848864Notes

Reaction equation

HRID 1848864 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-f6b0cbd5cba84ac29a09928d665d97bb
Source dataset
uspto-grants-2015_02
Patent number
US08952157B2

Reaction notes

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