2,4-Dichlorobenzoic Acid → BENZOIC ACID, 2-[(3-BROMOPHENYL)AMINO]-4-CHLORO-

HRID 1241689Notes

Reaction equation

HRID 1241689 reaction equation
Cl[C:2]1[CH:10]=[C:9]([Cl:11])[CH:8]=[CH:7][C:3]=1[C:4]([OH:6])=[O:5].[Br:12][C:13]1[CH:14]=[C:15]([CH:17]=[CH:18][CH:19]=1)[NH2:16].C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C.[Cu]>[Br:12][C:13]1[CH:14]=[C:15]([NH:16][C:2]2[CH:10]=[C:9]([Cl:11])[CH:8]=[CH:7][C:3]=2[C:4]([OH:6])=[O:5])[CH:17]=[CH:18][CH:19]=1

Participants

6

Reactant 3

HCID 57872,4-Dichlorobenzoic AcidHCID 11430Potassium CarbonateHCID 115623-Bromoaniline

Product 1

HCID 13400569BENZOIC ACID, 2-[(3-BROMOPHENYL)AMINO]-4-CHLORO-Yield 61.1%

Reagents, catalysts & solvents 2

HCID 23978CopperCatalystHCID 6228DimethylformamideSolvent

Conditions

Temperature
150 °C

Procedure

(Method D-2) Under an atmosphere of nitrogen, 2,4-dichlorobenzoic acid (36 g, 0.19 mol), 3-bromoaniline (48 g, 0.28 mol), potassium carbonate (32 g, 0.23 mol), and copper powder (1 g, 0.016 mol, catalytic) were mixed in dry DMF (150 ml) and heated to 150° C. for 18 hrs. The DMF was removed under reduced pressure, water (200 mL) added and the mixture acidified with 2M HCl (400 mL) to give a brown solid which was collected by filtration. Recrystallisation from ethanol/water (60/40) gave the title compound (43 g, 0.116 mol 61%) as a grey solid. See, for example, Hodgeman et al., 1972.

Workup

  1. customThe DMF was removed under reduced pressure, water (200 mL)
  2. additionadded
  3. customto give a brown solid which
  4. filtrationwas collected by filtration
  5. customRecrystallisation from ethanol/water (60/40)

Sources & evidence

ORD record
ord-25bf672522a741bc8df3d4a2ebb22511
Source dataset
uspto-grants-2006_10
Patent number
US07115619B2

Reaction notes

Loading…