4-Chlorophenylboronic acid → 3-[2-(4'-Chloro-1,1'-biphenyl-4-yl)ethyl]-1,3-oxazolidine-2,4-dione

HRID 1867535Notes

Reaction equation

HRID 1867535 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH2:9][N:10]2[C:14](=[O:15])[CH2:13][O:12][C:11]2=[O:16])=[CH:4][CH:3]=1.[Cl:17][C:18]1[CH:23]=[CH:22][C:21](B(O)O)=[CH:20][CH:19]=1.O.P([O-])([O-])([O-])=O.[K+].[K+].[K+]>COCCOC.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[Pd]>[Cl:17][C:18]1[CH:23]=[CH:22][C:21]([C:2]2[CH:7]=[CH:6][C:5]([CH2:8][CH2:9][N:10]3[C:14](=[O:15])[CH2:13][O:12][C:11]3=[O:16])=[CH:4][CH:3]=2)=[CH:20][CH:19]=1

Participants

6

Reactant 3

HCID 742994-Chlorophenylboronic acidHCID 22031701Potassium phosphate, tribasic, monohydrateHCID 675289483-[2-(4-Bromophenyl)ethyl]-1,3-oxazolidine-2,4-dione

Product 1

HCID 675285133-[2-(4'-Chloro-1,1'-biphenyl-4-yl)ethyl]-1,3-oxazolidine-2,4-dione

Reagents, catalysts & solvents 2

HCID 11979704Tetrakis(triphenylphosphine)palladiumCatalystHCID 80711,2-DimethoxyethaneSolvent

Procedure

A 250 ml three-necked round-bottomed flask placed under an inert atmosphere is charged with 2 g (7.04 mmol) of 3-[2-(4-bromophenyl)ethyl]-1,3-oxazolidine-2,4-dione, obtained in step 3.1., 2.2 g (14.08 mmol) of 4-chlorophenylboronic acid and 6.5 g (28.16 mmol) of potassium phosphate hydrate in suspension in 100 ml of 1,2-dimethoxyethane. Subsequently 0.80 g (0.70 mmol) of palladium tetrakis(triphenylphosphine) is added. The reaction mixture is subsequently refluxed overnight. The salts are separated by filtration over Celite and then the filtrate is concentrated under reduced pressure. The residue is taken up in ethyl acetate and water. The organic phase is separated and is washed with saturated aqueous sodium chloride solution. The filtrate is concentrated under reduced pressure and the residue is purified by chromatography on silica gel, eluting with dichloromethane.

Workup

  1. customA 250 ml three-necked round-bottomed flask placed under an inert atmosphere
  2. customobtained in step 3.1
  3. customThe salts are separated by filtration over Celite
  4. concentrationthe filtrate is concentrated under reduced pressure
  5. customThe organic phase is separated
  6. washis washed with saturated aqueous sodium chloride solution
  7. concentrationThe filtrate is concentrated under reduced pressure
  8. customthe residue is purified by chromatography on silica gel
  9. washeluting with dichloromethane

Sources & evidence

ORD record
ord-b6033f8aeb1040af830aaf00e75e3a75
Source dataset
uspto-grants-2009_12
Patent number
US07632850B2

Reaction notes

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