Hydrochloric Acid → HCID 57440925, compound

HRID 549481Notes

Reaction equation

HRID 549481 reaction equation
[N+:1]([C:4]1[CH:11]=[C:10]([Cl:12])[CH:9]=[CH:8][C:5]=1[CH:6]=O)([O-:3])=[O:2].[Br:13][C:14]1[CH:19]=[CH:18][C:17]([CH2:20][C:21]([OH:23])=[O:22])=[CH:16][CH:15]=1.C(OC(=O)C)(=O)C.C(=O)([O-])[O-].[K+].[K+].Cl>O>[Br:13][C:14]1[CH:15]=[CH:16][C:17](/[C:20](=[CH:6]\[C:5]2[CH:8]=[CH:9][C:10]([Cl:12])=[CH:11][C:4]=2[N+:1]([O-:3])=[O:2])/[C:21]([OH:23])=[O:22])=[CH:18][CH:19]=1

Participants

7

Reactant 5

HCID 313Hydrochloric AcidHCID 7918Acetic AnhydrideHCID 11430Potassium CarbonateHCID 74654Benzeneacetic acid, 4-bromo-HCID 796744-Chloro-2-nitrobenzaldehyde

Product 1

HCID 57440925HCID 57440925, compoundYield 58.1%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
100 °C

Procedure

A 2 L flask equipped with a mechanical stirrer was charged with 183 g of 2-nitro-4-chlorobenzaldehyde, 212 g of 4-bromophenylacetic acid and 233 mL of acetic anhydride. To this solution was added 82 g of potassium carbonate and the reaction was stirred overnight at 100° C. The resulting dark mixture was cooled down to room temperature and 1.6 L of water was added followed by 800 mL of 10% HCl. The solution was decanted and taken up in water/ethyl acetate. Layers were separated, organic phase was washed with brine, dried over magnesium sulphate and volatiles were removed under reduced pressure. The residue was triturated in EtOH and the mother liquor was triturated 4 more times with EtOH to afford 219 g of the desired (2E)-2-(4-bromophenyl)-3-(4-chloro-2-nitrophenyl)acrylic acid.

Workup

  1. customA 2 L flask equipped with a mechanical stirrer
  2. temperatureThe resulting dark mixture was cooled down to room temperature
  3. customThe solution was decanted
  4. customLayers were separated
  5. washorganic phase was washed with brine
  6. dry with materialdried over magnesium sulphate and volatiles
  7. customwere removed under reduced pressure
  8. customThe residue was triturated in EtOH
  9. customthe mother liquor was triturated 4 more times with EtOH

Sources & evidence

ORD record
ord-eea4f2219de747519cbcd53cddf64dd8
Source dataset
uspto-grants-2011_05
Patent number
US07943649B2

Reaction notes

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