Sodium Carbonate → 2-Chloro-4-(5-chloro-2-methoxyphenyl)benzoic acid

HRID 1023782Notes

Reaction equation

HRID 1023782 reaction equation
Br[C:2]1[CH:10]=[CH:9][C:5]([C:6]([OH:8])=[O:7])=[C:4]([Cl:11])[CH:3]=1.[Cl:12][C:13]1[CH:14]=[CH:15][C:16]([O:22][CH3:23])=[C:17]([CH:21]=1)C(O)=O.C(=O)([O-])[O-].[Na+].[Na+].O1CCOCC1>C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2].CO>[Cl:11][C:4]1[CH:3]=[C:2]([C:15]2[CH:14]=[C:13]([Cl:12])[CH:21]=[CH:17][C:16]=2[O:22][CH3:23])[CH:10]=[CH:9][C:5]=1[C:6]([OH:8])=[O:7]

Participants

7

Reactant 4

HCID 10340Sodium CarbonateHCID 312751,4-DioxaneHCID 769705-Chloro-o-anisic acidHCID 1088294-Bromo-2-chlorobenzoic acid

Product 1

HCID 532275772-Chloro-4-(5-chloro-2-methoxyphenyl)benzoic acidYield 79.2%

Reagents, catalysts & solvents 2

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)CatalystHCID 887MethanolSolvent

Procedure

4-bromo-2-chlorobenzoic acid (0.4 g), 5-chloro-2-methoxybenzoic acid (0.4 g), Pd(dppf)Cl2 (0.12 g), sodium carbonate (0.9 g), dioxan (15 ml) and methanol (5 ml) were charged to a flask and heated at reflux for 16 h. Cooled to room temp and filtered (hyflo). The filtrate was concentrated in vacuo, then dissolved in ethyl acetate. The suspension was made basic by addition of dilute NaOH. The aqueous layer was separated and acidified using 2M HCl, extracted with EtOAc, dried (MgSO4) and evaporated in vacuo to give the sub-title compound Yield 0.4 g

Workup

  1. temperatureheated
  2. temperatureat reflux for 16 h
  3. filtrationfiltered (hyflo)
  4. concentrationThe filtrate was concentrated in vacuo
  5. dissolutiondissolved in ethyl acetate
  6. additionThe suspension was made basic by addition of dilute NaOH
  7. customThe aqueous layer was separated
  8. extractionextracted with EtOAc
  9. dry with materialdried (MgSO4)
  10. customevaporated in vacuo

Sources & evidence

ORD record
ord-e52c56bab44c44fcbc7ae577f330430f
Source dataset
uspto-grants-2014_05
Patent number
US08722741B2

Reaction notes

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