Pyridine → HCID 19850901, compound

HRID 1607676Notes

Reaction equation

HRID 1607676 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([C:8](=[O:10])[CH3:9])=[CH:4][C:3]=1[O:11][C:12]1[CH:17]=[CH:16][C:15]([F:18])=[CH:14][C:13]=1[F:19].N1C=CC=CC=1.[Cl-:26].[Cl-].IC1C=CC=CC=1>O1CCCC1>[NH2:1][C:2]1[C:3]([O:11][C:12]2[CH:17]=[CH:16][C:15]([F:18])=[CH:14][C:13]=2[F:19])=[CH:4][C:5]([C:8](=[O:10])[CH3:9])=[CH:6][C:7]=1[Cl:26]

Participants

5

Reactant 3

HCID 1049PyridineHCID 10061288HCID 10061288, compoundHCID 13166207CID 13166207

Product 1

HCID 19850901HCID 19850901, compoundYield 78%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
5 °C

Procedure

A mixture of 4'-amino-3'-(2,4-difluorophenoxy)acetophenone (1.7 g), pyridine (0.52 g), and iodobenzene dichloride (1.8 g) in tetrahydrofuran (20 ml) was stirred overnight at 5° C. The mixture was concentrated. The residue was dissolved in ethyl acetate and washed with water, an aqueous solution of sodium bisulfite, and water. The organic layer was evaporated to give a powder of 4'-amino-3'-chloro-5'-(2,4-difluorophenoxy)acetophenone (1.5 g).

Workup

  1. concentrationThe mixture was concentrated
  2. dissolutionThe residue was dissolved in ethyl acetate
  3. washwashed with water
  4. customThe organic layer was evaporated

Sources & evidence

ORD record
ord-786de64811dc43e1af9dc7ec2c24c45e
Source dataset
uspto-grants-1989_09
Patent number
US04866091

Reaction notes

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