Acetic Acid → HCID 117620576, compound

HRID 626312Notes

Reaction equation

HRID 626312 reaction equation
[Br:1][C:2]1([Br:18])[CH2:4][CH:3]1[CH2:5][O:6][C:7]1[CH:12]=[C:11]([CH3:13])[C:10]([N+:14]([O-])=O)=[CH:9][C:8]=1[CH3:17].C(O)(=O)C>[Fe].O>[Br:1][C:2]1([Br:18])[CH2:4][CH:3]1[CH2:5][O:6][C:7]1[C:8]([CH3:17])=[CH:9][C:10]([NH2:14])=[C:11]([CH3:13])[CH:12]=1

Participants

5

Reactant 2

HCID 176Acetic AcidHCID 117620688HCID 117620688, compound

Product 1

HCID 117620576HCID 117620576, compoundYield 55.8%

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 962WaterSolvent

Conditions

Temperature
80 °C

Procedure

A mixture of 0.37 g of 1-[(2,2-dibromocyclopropyl)methoxy]-2,5-dimethyl-4-nitrobenzene, 0.29 g of iron powder, 20 mL of acetic acid and 5 mL of water was stirred at 80° C. for 1 hour. The reaction mixture was cooled to around room temperature, and then concentrated under reduced pressure. The resulting residue was converted into basic with an aqueous 1 N sodium hydroxide solution, then ethyl acetate was added, and the mixture was filtered. The filtrate was extracted with ethyl acetate, and then the organic layer was washed with water and saturated salt water, and dried over anhydrous magnesium sulfate. The resulting residue was subjected to silica gel column chromatography to obtain 0.19 g of 4-[(2,2-dibromocyclopropyl)methoxy]-2,5-dimethylphenylamine

Workup

  1. temperatureThe reaction mixture was cooled to around room temperature
  2. concentrationconcentrated under reduced pressure
  3. additionethyl acetate was added
  4. filtrationthe mixture was filtered
  5. extractionThe filtrate was extracted with ethyl acetate
  6. washthe organic layer was washed with water and saturated salt water
  7. dry with materialdried over anhydrous magnesium sulfate

Sources & evidence

ORD record
ord-01626728d14842228389d84a7e80f04e
Source dataset
uspto-grants-2016_04
Patent number
US09309191B2

Reaction notes

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