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Isobutyric Acid → Ethyl 2-(4-fluoro-3-nitrophenyl)-4-methyl-1,3-thiazole-5-carboxylate

HRID 1051304
ノート
印刷プレビュー

反応式

HRID 1051304 の反応式
C(=O)([O-])O.[K+].Br[C:7]1[CH:8]=[CH:9][C:10]([F:16])=[C:11]([N+:13]([O-:15])=[O:14])[CH:12]=1.[CH3:17][C:18]1[N:19]=[CH:20][S:21][C:22]=1[C:23]([O:25][CH2:26][CH3:27])=[O:24].C(O)(=O)C(C)C.C(P(C(C)(C)C)C1CCCCC1)(C)(C)C>C1(C)C=CC=CC=1.Cl[Pd]Cl.[Cu](Br)Br>[F:16][C:10]1[CH:9]=[CH:8][C:7]([C:20]2[S:21][C:22]([C:23]([O:25][CH2:26][CH3:27])=[O:24])=[C:18]([CH3:17])[N:19]=2)=[CH:12][C:11]=1[N+:13]([O-:15])=[O:14]
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

9

反応物 5

HCID 6590Isobutyric AcidHCID 2986105-Thiazolecarboxylic acid, 4-methyl-, ethyl esterHCID 516893Potassium BicarbonateHCID 27363284-Bromo-1-fluoro-2-nitrobenzeneHCID 4643321Di-tert-butylcyclohexylphosphine

生成物 1

HCID 118555037Ethyl 2-(4-fluoro-3-nitrophenyl)-4-methyl-1,3-thiazole-5-carboxylate
収率 73.5%

試薬・触媒・溶媒 3

HCID 24290Palladium Chloride触媒HCID 24611Copper bromide (CuBr2)触媒HCID 1140Toluene溶媒

反応条件

温度
120 °C

実験手順

A mixture was prepared by adding 2.10 g of potassium hydrogen carbonate, 44 mg of palladium chloride (II) and 205 mg of a copper bromide (I) dimethylsulfide complex to 2.20 g of 5-bromo-2-fluoronitrobenzene and the resulting mixture was suspended in 20 mL of toluene. Subsequently, a reaction mixture solution prepared by adding 2.05 g of ethyl 4-methyl-1,3-thiazole-5-carboxylate, 92.5 μL of isobutyric acid and 228 mg of di-t-butylcyclohexylphosphine to the resulting suspension was heated at 120° C. for 14 hours under a nitrogen atmosphere. The reaction mixture solution was celite-filtered to remove insoluble matter and water was added to the filtrate, and extraction was performed using ethyl acetate. The organic layer was washed with saline and dried and concentrated under reduced pressure. The resulting crude product was separated and purified by silica gel column chromatography to obtain 2.28 g of ethyl 2-(4-fluoro-3-nitrophenyl)-4-methyl-1,3-thiazole-5-carboxylate.

後処理

  1. customA mixture was prepared
  2. customSubsequently, a reaction mixture solution prepared
  3. filtrationThe reaction mixture solution was celite-filtered
  4. customto remove insoluble matter and water
  5. additionwas added to the filtrate, and extraction
  6. washThe organic layer was washed with saline
  7. customdried
  8. concentrationconcentrated under reduced pressure
  9. customThe resulting crude product was separated
  10. custompurified by silica gel column chromatography

出典と根拠

ORDレコード
ord-d31b808f8970403682c7aaac07b92084
出典データセット
uspto-grants-2016_07
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US09388174B2

反応ノート

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このページの内容参加物反応条件実験手順後処理出典と根拠反応ノート