Water → 2',3'-Dichloro-[1,1'-biphenyl]-3-acetic acid ethyl ester

HRID 1023282Notes

Reaction equation

HRID 1023282 reaction equation
[CH2:1]([O:3][C:4](=[O:13])[CH2:5][C:6]1[CH:11]=[CH:10][CH:9]=[C:8](I)[CH:7]=1)[CH3:2].[Cl:14][C:15]1[C:20]([Cl:21])=[CH:19][CH:18]=[CH:17][C:16]=1B(O)O.C(=O)(O)[O-].[Na+].O>O1CCOCC1.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[CH2:1]([O:3][C:4](=[O:13])[CH2:5][C:6]1[CH:7]=[C:8]([C:19]2[CH:18]=[CH:17][CH:16]=[C:15]([Cl:14])[C:20]=2[Cl:21])[CH:9]=[CH:10][CH:11]=1)[CH3:2]

Participants

7

Reactant 4

HCID 962WaterHCID 516892Sodium BicarbonateHCID 27346612,3-Dichlorobenzeneboronic acidHCID 57581611Ethyl 2-(3-iodophenyl)acetate

Product 1

HCID 669734082',3'-Dichloro-[1,1'-biphenyl]-3-acetic acid ethyl ester

Reagents, catalysts & solvents 2

HCID 178418476HCID 178418476, compoundCatalystHCID 312751,4-DioxaneSolvent

Procedure

A mixture of 3-iodobenzeneacetic acid ethyl ester (0.87 g, 3 mmol, prepared by the method described in J. Chem. Soc. 1963, 5437), 2,3-dichlorophenylboronic acid (0.85 g, 4.5 mmol), bis(triphenylphosphine)palladium dichloride (0.10 g, 0.15 mmol) and 2N aqueous sodium bicarbonate solution (3 mL) in p-dioxane (6 mL) was heated at 160° C. in a microwave reactor for 5 min. The reaction mixture was cooled, poured into water, and extracted with ethyl acetate. The organic layer was separated, washed with brine, dried over Na2SO4, and concentrated under reduced pressure. The residue was purified by chromatography on silica gel eluted with ethyl acetate in hexanes to provide the title product (0.48 g).

Workup

  1. customprepared by the method
  2. temperatureThe reaction mixture was cooled
  3. extractionextracted with ethyl acetate
  4. customThe organic layer was separated
  5. washwashed with brine
  6. dry with materialdried over Na2SO4
  7. concentrationconcentrated under reduced pressure
  8. customThe residue was purified by chromatography on silica gel
  9. washeluted with ethyl acetate in hexanes

Sources & evidence

ORD record
ord-c5ff627eef114a51a05d07387497d07d
Source dataset
uspto-grants-2014_05
Patent number
US08722690B2

Reaction notes

Loading…