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

HRID 1867535
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HRID 1867535 반응식
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
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참가 물질

6

반응물 3

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

생성물 1

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

시약·촉매·용매 2

HCID 11979704Tetrakis(triphenylphosphine)palladium
촉매
HCID 80711,2-Dimethoxyethane용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-b6033f8aeb1040af830aaf00e75e3a75
출처 데이터셋
uspto-grants-2009_12
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07632850B2

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