HCID 57440925, compound → HCID 57440926, compound

HRID 549482Notes

Reaction equation

HRID 549482 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5](/[C:8](=[CH:12]\[C:13]2[CH:18]=[CH:17][C:16]([Cl:19])=[CH:15][C:14]=2[N+:20]([O-])=O)/[C:9]([OH:11])=[O:10])=[CH:4][CH:3]=1>C(O)(=O)C.O.C(OCC)(=O)C.[Fe]>[NH2:20][C:14]1[CH:15]=[C:16]([Cl:19])[CH:17]=[CH:18][C:13]=1/[CH:12]=[C:8](\[C:5]1[CH:4]=[CH:3][C:2]([Br:1])=[CH:7][CH:6]=1)/[C:9]([OH:11])=[O:10]

Participants

6

Reactant 1

HCID 57440925HCID 57440925, compound

Product 1

HCID 57440926HCID 57440926, compoundYield 104.5%

Reagents, catalysts & solvents 4

HCID 23925IronCatalystHCID 176Acetic AcidSolventHCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
50 °C

Procedure

To a 50° C. solution of 135 g of (2E)-2-(4-bromophenyl)-3-(4-chloro-2-nitrophenyl)acrylic acid from Step 1 in 1.2 L of acetic acid and 80 mL of water, was added 98 g of iron (powder) portion wise maintaining the temperature below 50° C. The mixture was stirred 2 hrs at 50° C., cooled down to room temperature, diluted with ethyl acetate (1 L) and filtered through a plug of celite. Water (1 L) was added, the layers were separated and the organic layer was washed 2 times with water, brine, dried over magnesium sulphate and volatiles were removed under reduced pressure. Residual acetic acid was removed by the addition of 1 L of H2O to the crude mixture, the solution was filtered and washed with an additional 1 L of H2O and finally the solid was dried under high vacuum to afford 130 g of (2E)-3-(2-amino-4-chlorophenyl)-2-(4-bromophenyl)acrylic acid.

Workup

  1. temperaturewise maintaining the temperature below 50° C
  2. temperaturecooled down to room temperature
  3. filtrationfiltered through a plug of celite
  4. additionWater (1 L) was added
  5. customthe layers were separated
  6. washthe organic layer was washed 2 times with water, brine
  7. dry with materialdried over magnesium sulphate and volatiles
  8. customwere removed under reduced pressure
  9. customResidual acetic acid was removed by the addition of 1 L of H2O to the crude mixture
  10. filtrationthe solution was filtered
  11. washwashed with an additional 1 L of H2O
  12. customfinally the solid was dried under high vacuum

Sources & evidence

ORD record
ord-7cc42bdad0ac4506b53ec2aedde0de3e
Source dataset
uspto-grants-2011_05
Patent number
US07943649B2

Reaction notes

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