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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
ノート
印刷プレビュー

反応式

HRID 1867535 の反応式
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
参加物実験手順後処理出典と根拠反応ノート

参加物

6

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 11979704Tetrakis(triphenylphosphine)palladium
触媒
HCID 80711,2-Dimethoxyethane溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-b6033f8aeb1040af830aaf00e75e3a75
出典データセット
uspto-grants-2009_12
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US07632850B2

反応ノート

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