Water → HCID 19744233, compound

HRID 2254112Notes

Reaction equation

HRID 2254112 reaction equation
[Br:1][C:2]1[C:3]([O:12][C:13]([F:18])([F:17])[CH:14]([F:16])[F:15])=[CH:4][C:5]([N+:9]([O-])=O)=[C:6]([CH:8]=1)[NH2:7].[N+](C1C=CC=CC=1N)([O-])=O.BrBr.O>C(OCC)(=O)C.C(O)(=O)C.[Fe]>[Br:1][C:2]1[CH:8]=[C:6]([NH2:7])[C:5]([NH2:9])=[CH:4][C:3]=1[O:12][C:13]([F:18])([F:17])[CH:14]([F:15])[F:16]

Participants

8

Reactant 4

HCID 962WaterHCID 69462-NitroanilineHCID 24408BromineHCID 19744225HCID 19744225, compound

Product 1

HCID 19744233HCID 19744233, compound

Reagents, catalysts & solvents 3

HCID 23925IronCatalystHCID 176Acetic AcidSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

10.5 Grams of 5-bromo-2-nitro-4-(1',1',2',2'-tetrafluoroethoxy)aniline [i.e. the o-nitroaniline compound (VI) containing bromine as the substituent X] was dissolved in a mixed solvent of 25 ml of ethyl acetate and 25 ml of acetic acid. The resulting solution was dropwise added to a suspension of 5.0 g of iron powders in a mixed solution of 7 ml of acetic acid and 50 ml of water while maintaining the temperature at 45°-70° C. Thereafter, stirring was continued for 10 minutes within the same temperature range. The reaction solution was filtered through Celite, and the filtrate was extracted with ethyl acetate. The organic layer was washed with an aqueous sodium hydrogencarbonate solution and water in this order, dried over anhydrous magnesium sulfate and concentrated to obtain 9.5 g of 4-bromo-5-(1',1',2',2'-tetrafluoroethoxy) -1,2-benzenediamine. 1H-NMR (CDCl3): δ(ppm) 6.78(1H, s), 6.60(1H), 5.90(1H, tt, J=3, 52 Hz), 3.45(4H, broad)

Workup

  1. temperaturewhile maintaining the temperature at 45°-70° C
  2. filtrationThe reaction solution was filtered through Celite
  3. extractionthe filtrate was extracted with ethyl acetate
  4. washThe organic layer was washed with an aqueous sodium hydrogencarbonate solution and water in this order
  5. dry with materialdried over anhydrous magnesium sulfate
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-e0ab4d2d2791411586bb9e9e19db6eff
Source dataset
uspto-grants-1993_08
Patent number
US05234938

Reaction notes

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