Ammonium Chloride → HCID 118143193, compound

HRID 523958Notes

Reaction equation

HRID 523958 reaction equation
[N+:1]([C:4]1[C:5]([Br:16])=[C:6]([Cl:15])[C:7]2[O:11][C:10]([F:13])([F:12])[O:9][C:8]=2[CH:14]=1)([O-])=O.[Cl-].[NH4+]>C(O)C.O.[Fe]>[NH2:1][C:4]1[C:5]([Br:16])=[C:6]([Cl:15])[C:7]2[O:11][C:10]([F:13])([F:12])[O:9][C:8]=2[CH:14]=1

Participants

6

Reactant 2

HCID 25517Ammonium ChlorideHCID 118143211HCID 118143211, compound

Product 1

HCID 118143193HCID 118143193, compoundYield 100%

Reagents, catalysts & solvents 3

HCID 23925IronCatalystHCID 702EthanolSolventHCID 962WaterSolvent

Conditions

Temperature
90 °C

Procedure

To the slurry of 6-nitro-5-bromo-4-chloro-2,2-diflouro-1,3-benzodioxole (1.0 g, 3.16 mmol) in ethanol (4 mL) and water (1 mL) was added ammonium chloride (3.38 g, 63.2 mmol) and iron powder (1.06 g, 18.96 mmol). The mixture was warmed up to 90° C. for 1 h and then cooled down. Filtered through a Celite plug and concentrated in vacuo. The crude product was purified by flash chromatography (SiO2, 0-30% ethyl acetate in hexanes) to afford 6-amino-5-bromo-4-chloro-2,2-diflouro-1,3-benzodioxole as a white solid (0.90 g, 3.16 mmol, 100%). MS: (ES) m/z calculated for C7H3BrClF2NO2 [M+H]+286.0. found 286.

Workup

  1. temperaturecooled down
  2. filtrationFiltered through a Celite plug
  3. concentrationconcentrated in vacuo
  4. customThe crude product was purified by flash chromatography (SiO2, 0-30% ethyl acetate in hexanes)

Sources & evidence

ORD record
ord-612ecde247764f5892c2d1aac8131732
Source dataset
uspto-grants-2016_05
Patent number
US09340509B2

Reaction notes

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