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Cerium(III) chloride → 5-Bromo-2-chlorophenyl 6-ethyl-3-pyridyl ketone

HRID 1625899
ノート
印刷プレビュー

反応式

HRID 1625899 の反応式
Br[C:2]1[N:7]=[CH:6][C:5]([C:8]([C:10]2[CH:15]=[C:14]([Br:16])[CH:13]=[CH:12][C:11]=2[Cl:17])=[O:9])=[CH:4][CH:3]=1.[CH2:18]([Al](CC)CC)[CH3:19].[Cl-].[Ce+3].[Cl-].[Cl-].C(=O)([O-])O.[Na+]>O1CCCC1.CO.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>[CH2:18]([C:2]1[N:7]=[CH:6][C:5]([C:8]([C:10]2[CH:15]=[C:14]([Br:16])[CH:13]=[CH:12][C:11]=2[Cl:17])=[O:9])=[CH:4][CH:3]=1)[CH3:19]
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

8

反応物 4

HCID 24636Cerium(III) chlorideHCID 516892Sodium BicarbonateHCID 16682930TriethylaluminumHCID 469303355-Bromo-2-chlorophenyl 6-bromo-3-pyridyl ketone

生成物 1

HCID 469305245-Bromo-2-chlorophenyl 6-ethyl-3-pyridyl ketone

試薬・触媒・溶媒 3

HCID 178418397
HCID 178418397、化合物
触媒
HCID 887Methanol溶媒
HCID 8028Tetrahydrofuran溶媒

反応条件

温度
30 °C

実験手順

5-Bromo-2-chlorophenyl 6-bromo-3-pyridyl ketone (3.2 g) from Reference Example 135-(2) was dissolved in tetrahydrofuran (80 ml), and added thereto were triethylaluminium (1.0 M hexane solution, 9.9 ml), tetrakis(triphenylphosphine)palladium(0) (570 mg) and cerium(III) chloride (7.3 g), and the mixture was stirred at 30° C. for 1.5 hours. The reaction mixture was diluted with methanol, and the reaction solution was basified with a saturated aqueous sodium hydrogen carbonate solution. The insoluble materials were filtered off and, the filtrate was extracted with ethyl acetate and dried over magnesium sulfate. The solvent was evaporated under reduced pressure, and the residue was purified by silica gel column chromatography (hexane:ethyl acetate=99:1-85:15) to give 5-bromo-2-chlorophenyl 6-ethyl-3-pyridyl ketone (1.98 g) as a colorless solid. APCI-Mass m/Z 324/326 (M+H).

後処理

  1. additionadded
  2. filtrationThe insoluble materials were filtered off
  3. extractionthe filtrate was extracted with ethyl acetate
  4. dry with materialdried over magnesium sulfate
  5. customThe solvent was evaporated under reduced pressure
  6. customthe residue was purified by silica gel column chromatography (hexane:ethyl acetate=99:1-85:15)

出典と根拠

ORDレコード
ord-c2a76b2f07c14be89bdb805626d87be4
出典データセット
uspto-grants-2014_07
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08785403B2

反応ノート

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