Sodium Carbonate → HCID 90462987, compound

HRID 588836Notes

Reaction equation

HRID 588836 reaction equation
[Cl:1][C:2]1[C:11](I)=[CH:10][C:5]([C:6]([O:8][CH3:9])=[O:7])=[C:4]([O:13][CH3:14])[CH:3]=1.[Cl:15][C:16]1[CH:21]=[CH:20][C:19]([Cl:22])=[CH:18][C:17]=1B(O)O.C([O-])([O-])=O.[Na+].[Na+]>O1CCOCC1.O.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[Cl:15][C:16]1[CH:21]=[CH:20][C:19]([Cl:22])=[CH:18][C:17]=1[C:11]1[C:2]([Cl:1])=[CH:3][C:4]([O:13][CH3:14])=[C:5]([C:6]([O:8][CH3:9])=[O:7])[CH:10]=1

Participants

7

Reactant 3

HCID 10340Sodium CarbonateHCID 27733712,5-Dichlorobenzeneboronic acidHCID 86767743HCID 86767743, compound

Product 1

HCID 90462987HCID 90462987, compoundYield 85%

Reagents, catalysts & solvents 3

HCID 178418397HCID 178418397, compoundCatalystHCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Procedure

A mixture of Methyl 4-chloro-5-iodo-2-methoxybenzoate (1.8 g, 5.51 mmol), (2,5-dichlorophenyl)boronic acid (2.1 g, 11.03 mmol), Pd(PPh3)4 (403 mg, 0.55 mmol), Na2CO3 (1.75 g, 16.54 mmol) in 1,4-dioxane (50 mL) and water (5 mL) was stirred at reflux under argon for 16 h. The mixture was filtered and filtrate was concentrated in vacuo. The residue was purified by flash column chromatography on silica gel (petroleum ether/ethyl acetate=20:1) to afford the desired product (1.6 g, 85% yield).

Workup

  1. temperatureat reflux under argon for 16 h
  2. filtrationThe mixture was filtered
  3. concentrationfiltrate was concentrated in vacuo
  4. customThe residue was purified by flash column chromatography on silica gel (petroleum ether/ethyl acetate=20:1)

Sources & evidence

ORD record
ord-b3795de29c2f4c45974615f23f6781da
Source dataset
uspto-grants-2016_01
Patent number
US09227978B2

Reaction notes

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