Ethyl Acetate → (4-Chloro-phenyl)-(4,5-difluoro-2-iodo-phenyl)-diazene

HRID 1690536Notes

Reaction equation

HRID 1690536 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]=O)=[CH:4][CH:3]=1.[F:10][C:11]1[C:16]([F:17])=[CH:15][C:14]([NH2:18])=[C:13]([I:19])[CH:12]=1.CCOC(C)=O>C(O)(=O)C>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]=[N:18][C:14]2[CH:15]=[C:16]([F:17])[C:11]([F:10])=[CH:12][C:13]=2[I:19])=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 8857Ethyl AcetateHCID 136141-Chloro-4-nitrosobenzeneHCID 121819134,5-Difluoro-2-iodoaniline

Product 1

HCID 86640263(4-Chloro-phenyl)-(4,5-difluoro-2-iodo-phenyl)-diazeneYield 27%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

Chloro-4-nitroso-benzene (9.1 g, 64 mmol; [932-98-9]) was added to a solution of 4,5-difluoro-2-iodo-phenylamine (10.9 g, 43 mmol; [847685-01-2]) in acetic acid (430 ml). The reaction mixture was heated under reflux conditions for 14 h. Ice water (1 l) and EtOAc (1 l) was added, the layers were separated and the aqueous layer was extracted two times with EtOAc. The combined extracts were washed with water and brine and dried over Na2SO4. The solvent was removed under reduced pressure and the residue was purified by column chromatography (silica gel, CH2Cl2/heptane) to give the title compound (4.34 g, 11 mmol; 27%) as orange solid. MS: m/e=377.9 [M+].

Workup

  1. temperatureThe reaction mixture was heated under reflux conditions for 14 h
  2. customthe layers were separated
  3. extractionthe aqueous layer was extracted two times with EtOAc
  4. washThe combined extracts were washed with water and brine
  5. dry with materialdried over Na2SO4
  6. customThe solvent was removed under reduced pressure
  7. customthe residue was purified by column chromatography (silica gel, CH2Cl2/heptane)

Sources & evidence

ORD record
ord-573ef9d7b8a340d18c5bc0e62fae1cba
Source dataset
uspto-grants-2012_04
Patent number
US08153663B2

Reaction notes

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