Potassium Carbonate → HCID 69218742, compound

HRID 272667Notes

Reaction equation

HRID 272667 reaction equation
[Cl:1][C:2]1[CH:11]=[CH:10][C:5]([C:6]([O:8][CH3:9])=[O:7])=[C:4](I)[CH:3]=1.[Br:13][C:14]1[CH:20]=[CH:19][C:17]([NH2:18])=[C:16]([N+:21]([O-:23])=[O:22])[CH:15]=1.C([O-])([O-])=O.[K+].[K+]>ClC1C=CC=CC=1.C(OCC)(=O)C.[Cu]>[Br:13][C:14]1[CH:20]=[CH:19][C:17]([NH:18][C:4]2[CH:3]=[C:2]([Cl:1])[CH:11]=[CH:10][C:5]=2[C:6]([O:8][CH3:9])=[O:7])=[C:16]([N+:21]([O-:23])=[O:22])[CH:15]=1

Participants

7

Reactant 3

HCID 11430Potassium CarbonateHCID 701324-Bromo-2-nitroanilineHCID 123491904-Chloro-2-iodo-benzoic acid Methyl ester

Product 1

HCID 69218742HCID 69218742, compoundYield 89%

Reagents, catalysts & solvents 3

HCID 23978CopperCatalystHCID 7964ChlorobenzeneSolventHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of methyl 4-chloro-2-iodobenzoate (5.93 g, 20 mmol), 4-bromo-2-nitroaniline (4.34 g, 20 mmol), copper (1.26 g, 20 mmol), and K2CO3 (2.76 g, 20 mmol) in chlorobenzene (300 mL) was heated to reflux for 2 days, cooled to room temperature, diluted with ethyl acetate, and filtered through diatomaceous earth (Celite®). The solution was washed with water and brine, dried (MgSO4), filtered, and concentrated under vacuum. The residue was purified by flash column chromatography on silica gel with 9:1 hexanes/ethyl acetate to provide 6.86 g (89%) of the desired product. MS (DCI) m/e 386 (M+H)+, 403 (M+NH4)+; 1H NMR (300 MHz, DMSO-d6) δ 10.83 (s, 1H), 8.28 (d, J=2.4 Hz, 1H), 7.97 (d, J=8.5 Hz, 1H), 7.82 (dd, J=9.1, 2.4 Hz, 1H), 7.63 (d, J=9.1 Hz, 1H), 7.52 (d, J=2.1 Hz, 1H), 7.17 (dd, J=8.5, 2 Hz, 1H), 3.87 (s, 3H).

Workup

  1. temperaturewas heated
  2. temperatureto reflux for 2 days
  3. filtrationfiltered through diatomaceous earth (Celite®)
  4. washThe solution was washed with water and brine
  5. dry with materialdried (MgSO4)
  6. filtrationfiltered
  7. concentrationconcentrated under vacuum
  8. customThe residue was purified by flash column chromatography on silica gel with 9:1 hexanes/ethyl acetate

Sources & evidence

ORD record
ord-6cc5c018175047dbaf60ade739f54648
Source dataset
uspto-grants-2008_11
Patent number
US07456169B2

Reaction notes

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