Water → 1305341-02-9

HRID 1898231Notes

Reaction equation

HRID 1898231 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([N+:8]([O-])=O)=[CH:4][C:3]=1[C:11]([F:14])([F:13])[CH3:12].[Cl-].[NH4+].O>[Fe].CO>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([NH2:8])=[CH:4][C:3]=1[C:11]([F:13])([F:14])[CH3:12]

Participants

6

Reactant 3

HCID 962WaterHCID 25517Ammonium ChlorideHCID 58268055HCID 58268055, compound

Product 1

HCID 582682161305341-02-9Yield 87.8%

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 887MethanolSolvent

Conditions

Temperature
70 °C

Procedure

480 mg (2.17 mmol) of 1-chloro-2-(1,1-difluoro-ethyl)-4-nitro-benzene, 464 mg (8.67 mmol) of ammonium chloride and 365 mg (6.51 mmol) of iron powder were added to a mixture of 1.5 mL of water and 3 mL of methanol. The slurry was stirred at 70° C. for 1 h, and then cooled down, filtered through a pad of celite washing with excess methanol and concentrated down under reduced pressure. The residue was dissolved in ethyl acetate, evaporated under reduced pressure on silica gel and purified on silica eluting with a 5-30% ethyl acetate in hexanes to give 365 mg of the pure product as a white solid. LC-MSD, m/z for C8H8ClF2N [M+H]+=192.0, 194.0;

Workup

  1. temperaturecooled down
  2. filtrationfiltered through a pad of celite
  3. washwashing with excess methanol
  4. concentrationconcentrated down under reduced pressure
  5. dissolutionThe residue was dissolved in ethyl acetate
  6. customevaporated under reduced pressure on silica gel
  7. custompurified on silica eluting with a 5-30% ethyl acetate in hexanes

Sources & evidence

ORD record
ord-c34b5f6613054cf09f8af6ef9bd113d9
Source dataset
uspto-grants-2013_08
Patent number
US08519135B2

Reaction notes

Loading…