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Phosphorus tribromide → 1-[4'-(4-Bromomethyl-3-methyl-isoxazol-5-yl)-biphenyl-4-yl]-cyclopropanecarboxylic acid ethyl ester

HRID 1183272
ノート
印刷プレビュー

反応式

HRID 1183272 の反応式
P(Br)(Br)[Br:2].[CH2:5]([O:7][C:8]([C:10]1([C:13]2[CH:18]=[CH:17][C:16]([C:19]3[CH:24]=[CH:23][C:22]([C:25]4[O:29][N:28]=[C:27]([CH3:30])[C:26]=4[CH2:31]O)=[CH:21][CH:20]=3)=[CH:15][CH:14]=2)[CH2:12][CH2:11]1)=[O:9])[CH3:6].C([O-])(O)=O.[Na+]>COCCOC>[CH2:5]([O:7][C:8]([C:10]1([C:13]2[CH:18]=[CH:17][C:16]([C:19]3[CH:24]=[CH:23][C:22]([C:25]4[O:29][N:28]=[C:27]([CH3:30])[C:26]=4[CH2:31][Br:2])=[CH:21][CH:20]=3)=[CH:15][CH:14]=2)[CH2:12][CH2:11]1)=[O:9])[CH3:6]
参加物実験手順後処理出典と根拠反応ノート

参加物

5

反応物 3

HCID 24614Phosphorus tribromideHCID 516892Sodium BicarbonateHCID 665772181-[4'-(4-Hydroxymethyl-3-methyl-isoxazol-5-yl)-biphenyl-4-yl]-cyclopropanecarboxylic acid ethyl ester

生成物 1

HCID 665771991-[4'-(4-Bromomethyl-3-methyl-isoxazol-5-yl)-biphenyl-4-yl]-cyclopropanecarboxylic acid ethyl ester

試薬・触媒・溶媒 1

HCID 80711,2-Dimethoxyethane
溶媒

実験手順

Phosphorus tribromide (0.43 mL, 4.53 mmol) was added to a solution of 1-[4′-(4-hydroxymethyl-3-methyl-isoxazol-5-yl)-biphenyl-4-yl]-cyclopropanecarboxylic acid ethyl ester (1.14 g, 3.02 mmol) in DME (30 mL) at 0° C. The reaction was stirred overnight at room temperature, and then cooled to 0° C. and neutralized with saturated aqueous NaHCO3 to pH 7. The mixture was partitioned between CH2Cl2 and H2O, and the aqueous layer was extracted with CH2Cl2. The combined organic layers were dried over MgSO4, filtered, and concentrated, and the residue was purified by silica gel chromatography to give the title compound.

後処理

  1. customThe mixture was partitioned between CH2Cl2 and H2O
  2. extractionthe aqueous layer was extracted with CH2Cl2
  3. dry with materialThe combined organic layers were dried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customthe residue was purified by silica gel chromatography

出典と根拠

ORDレコード
ord-0d39e51113834f83854db4451e3e06ae
出典データセット
uspto-grants-2014_03
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08664220B2

反応ノート

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