Hydrochloric Acid → 93484-84-5

HRID 1417558Notes

Reaction equation

HRID 1417558 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([CH:10]=[C:11]([N+]([O-])=O)[CH3:12])[CH:5]=[CH:6][C:7]=1[O:8][CH3:9].O.Cl.C(OCC)(=[O:20])C>C1(C)C=CC=CC=1.[Fe]>[Br:1][C:2]1[CH:3]=[C:4]([CH2:10][C:11]([CH3:12])=[O:20])[CH:5]=[CH:6][C:7]=1[O:8][CH3:9]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 8857Ethyl AcetateHCID 53843028HCID 53843028, compound

Product 1

HCID 1869927193484-84-5

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 1140TolueneSolvent

Conditions

Temperature
80 °C

Procedure

A solution of 790 mg (2.90 mmol) of 1-(3-bromo-4-methoxyphenyl)-2-nitropropene (from Example 80, Step A) in 5.0 mL of toluene was combined with water (2.0 mL), iron powder (730 mg, 13.45 mmol), and ferric chloride (14.2 mg, 0.088 mmol) in a 25-mL three-neck round bottom flask fitted with a mechanical stirrer and reflux condenser. With vigorous agitation, the suspension was heated at 80° C., and 1.3 mL of conc. HCl was added over a period of 2 h via syringe. After the addition was completed, the heating and stirring were continued for an additional 30 min. After the reaction had cooled to RT, ethyl acetate (50 mL) was added to the solid was removed by filtration. The filtrate was washed with 20 mL of saturated aqueous sodium bicarbonate and the layers were separated. The aqueous layer was filtered again and the filtrate was extracted with 2×40 mL of ethyl acetate. The combined ethyl acetate extracts were washed with 50 mL of brine. Drying over sodium sulfate and concentration afforded a red oil which was purified by flash column chromatography, eluting with 30% dichloromethane in hexane followed by dichloromethane, to give 411 mg of the title compound as a yellow syrup.

Workup

  1. customfitted with a mechanical stirrer
  2. temperaturereflux condenser
  3. additionAfter the addition
  4. temperatureAfter the reaction had cooled to RT
  5. customwas removed by filtration
  6. washThe filtrate was washed with 20 mL of saturated aqueous sodium bicarbonate
  7. customthe layers were separated
  8. filtrationThe aqueous layer was filtered again
  9. extractionthe filtrate was extracted with 2×40 mL of ethyl acetate
  10. washThe combined ethyl acetate extracts were washed with 50 mL of brine
  11. dry with materialDrying over sodium sulfate and concentration
  12. customafforded a red oil which
  13. customwas purified by flash column chromatography
  14. washeluting with 30% dichloromethane in hexane

Sources & evidence

ORD record
ord-9f91fa4dbb244f10921bfa2a6ff7263a
Source dataset
uspto-grants-1999_03
Patent number
US05877191

Reaction notes

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