1-Bromo-2,4-dimethyl-3-nitrobenzene → HCID 12792330, compound

HRID 2105286Notes

Reaction equation

HRID 2105286 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([CH3:8])=[C:4]([N+:9]([O-])=O)[C:3]=1[CH3:12]>C(O)(=O)C.C(OCC)C.[Fe]>[Br:1][C:2]1[C:3]([CH3:12])=[C:4]([NH2:9])[C:5]([CH3:8])=[CH:6][CH:7]=1

Participants

5

Reactant 1

HCID 27533801-Bromo-2,4-dimethyl-3-nitrobenzene

Product 1

HCID 12792330HCID 12792330, compound

Reagents, catalysts & solvents 3

HCID 23925IronCatalystHCID 176Acetic AcidSolventHCID 3283Diethyl EtherSolvent

Conditions

Temperature
80 °C

Procedure

To a solution of crude 1-bromo-2,4-dimethyl-3-nitrobenzene (0.58 g, 2.9 mmol) in glacial acetic acid (12 mL) was added iron powder (0.65 g, 11.6 mmol). The mixture was stirred rapidly at 80° C. under nitrogen for 2 hours. Upon completion, the mixture was cooled, diluted with diethyl ether and extracted with aqueous sodium hydroxide solution (2N). The organic layer was dried over sodium sulfate, decanted and concentrated under reduced pressure to give 3-bromo-2,6-dimethylphenylamine as a yellow oil which was used without further purification.

Workup

  1. temperatureUpon completion, the mixture was cooled
  2. extractionextracted with aqueous sodium hydroxide solution (2N)
  3. dry with materialThe organic layer was dried over sodium sulfate
  4. customdecanted
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-e7713b99876e4fbba8fd1277b8d56e53
Source dataset
uspto-grants-2009_08
Patent number
US07579340B2

Reaction notes

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