4-Bromobenzaldehyde → 4'-Chloro[1,1'-biphenyl]-4-carbaldehyde

HRID 539850

反応式

HRID 539850 の反応式
[Cl:1][C:2]1[CH:7]=[CH:6][C:5](B(O)O)=[CH:4][CH:3]=1.Br[C:12]1[CH:19]=[CH:18][C:15]([CH:16]=[O:17])=[CH:14][CH:13]=1>C([O-])(=O)C.[Pd+2].C([O-])(=O)C.C(COC)OC>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:12]2[CH:19]=[CH:18][C:15]([CH:16]=[O:17])=[CH:14][CH:13]=2)=[CH:4][CH:3]=1

参加物

5

反応物 2

HCID 707414-BromobenzaldehydeHCID 742994-Chlorophenylboronic acid

生成物 1

HCID 5925704'-Chloro[1,1'-biphenyl]-4-carbaldehyde収率 94%

試薬・触媒・溶媒 2

HCID 167845palladium(II) acetate触媒HCID 80711,2-Dimethoxyethane溶媒

実験手順

A mixture of 4-chlorobenzeneboronic acid (19.4 g, 1 equiv), 4-bromobenzaldehyde (22.9 g, 1 equiv), palladium(II) acetate (1.4 g, 0.05 equiv) aqueous sodium carbonate (30.3 g in 144 ml solution, 2 equiv) and dimethoxyethane (500 ml) was stirred at reflux under argon for 2.5 h, then evaporated to low volume and diluted with dichloromethane. Workup continued as in (a) above to give identical material (25.2 g, 94%). 1H-NMR (CDCl3) δ 10.05 (1H, s), 7.96 (2H, d), 7.73 (2H, d), 7.57 (2H, d), 7.46 (2H, d); MS (AP+) found (M+1)=217, C13H935ClO requires 216.

後処理

  1. temperatureat reflux under argon for 2.5 h
  2. customevaporated to low volume
  3. additiondiluted with dichloromethane

出典と根拠

ORDレコード
ord-ac0c4465c37549558f992d061d6115f1
出典データセット
uspto-grants-2014_10
特許番号
US08871775B2

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