Water → 4-Hydroxy-(1,1'-biphenyl)-3-carbaldehyde

HRID 1043694

反応式

HRID 1043694 の反応式
[C:1]1(B(O)O)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C(Cl)Cl.[C:13]([O-:16])([O-])=O.[Na+].[Na+].[OH2:19]>COCCOC.O.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2]>[OH:19][C:1]1[CH:6]=[CH:5][C:4]([C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)=[CH:3][C:2]=1[CH:13]=[O:16]

参加物

7

反応物 4

HCID 962WaterHCID 6344DichloromethaneHCID 10340Sodium CarbonateHCID 66827Phenylboronic Acid

生成物 1

HCID 122646584-Hydroxy-(1,1'-biphenyl)-3-carbaldehyde収率 50%

試薬・触媒・溶媒 2

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)触媒HCID 18180031Water 1,2-dimethoxyethane溶媒

反応条件

温度
100 °C

実験手順

(Fahmy, A. M.; Revue Roumaine de Chimie 1985, V30(8), P749-52) Bromosalicaldehyde (S1, 525 mg, 2.6 mmol), phenylboronic acid (S2, 349 mg, 2.86 mmol), Pd(dppf)Cl2.CH2Cl2 (106 mg, 0.13 mmol) and Na2CO3 (413 mg, 3.9 mmol) were dissolved in degassed DME/H2O (3:1) and stirred at reflux (100° C.) for 5 h. After cooling, the mixture was poured into water and extracted with DCM (3×100 ml). The combined organic layers were dried over Na2SO4 and the residue purified by silica gel chromatography (Et2O, 100%) to afford the title compound (250 mg, 50%).

後処理

  1. temperatureAfter cooling
  2. extractionextracted with DCM (3×100 ml)
  3. dry with materialThe combined organic layers were dried over Na2SO4
  4. customthe residue purified by silica gel chromatography (Et2O, 100%)

出典と根拠

ORDレコード
ord-e81718c76b784abb83d3e438479e8b3f
出典データセット
uspto-grants-2013_10
特許番号
US08563557B2

関連ノート

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