Water → HCID 117607164, compound

HRID 588801Notes

Reaction equation

HRID 588801 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6](I)[C:5]([I:9])=[CH:4][C:3]=1[Cl:10].[OH:11][C:12]1[CH:13]=[C:14](B(O)O)[CH:15]=[CH:16][CH:17]=1.C([O-])([O-])=O.[Na+].[Na+].O>O1CCOCC1.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:10][C:3]1[C:2]([Cl:1])=[CH:7][C:6]([C:16]2[CH:17]=[C:12]([OH:11])[CH:13]=[CH:14][CH:15]=2)=[C:5]([I:9])[CH:4]=1

Participants

7

Reactant 4

HCID 962WaterHCID 10340Sodium CarbonateHCID 1446064,5-Dichloro-1,2-diiodobenzeneHCID 2734359(3-hydroxyphenyl)boronic Acid

Product 1

HCID 117607164HCID 117607164, compoundYield 22%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 312751,4-DioxaneSolvent

Procedure

A mixture of 1,2-dichloro-4,5-diiodobenzene (1.5 g, 3.76 mmol), 3-hydroxyphenylboronic acid (0.52 g, 3.76 mmol), Na2CO3 (1.99 g, 18.8 mmol) and Pd(PPh3)4 (0.35 g, 0.30 mmol), in 1,4-dioxane (10 mL) and water (2 mL) was stirred at reflux under argon for 16 h. The mixture was allowed to cool to room temperature and then 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 (300 mg, 22% yield). ESI-MS m/z: 362.9 [M−H]−.

Workup

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

Sources & evidence

ORD record
ord-c86b1cbdbfb14245b7a9ddaf8614ca02
Source dataset
uspto-grants-2016_01
Patent number
US09227978B2

Reaction notes

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