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Triethylamine → 5'-Methoxycarbonyl-2'-methylbiphenyl-4-carboxylic acid

HRID 1741053
ノート
印刷プレビュー

反応式

HRID 1741053 の反応式
Br[C:2]1[CH:3]=[C:4]([CH:9]=[CH:10][C:11]=1[CH3:12])[C:5]([O:7][CH3:8])=[O:6].B([C:16]1[CH:24]=[CH:23][C:19]([C:20]([OH:22])=[O:21])=[CH:18][CH:17]=1)(O)O.C(N(CC)CC)C>CN(C=O)C.[Pd].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>[CH3:8][O:7][C:5]([C:4]1[CH:9]=[CH:10][C:11]([CH3:12])=[C:2]([C:16]2[CH:24]=[CH:23][C:19]([C:20]([OH:22])=[O:21])=[CH:18][CH:17]=2)[CH:3]=1)=[O:6]
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

6

反応物 3

HCID 8471TriethylamineHCID 3121834-Carboxyphenylboronic AcidHCID 7015747Methyl 3-bromo-4-methylbenzoate

生成物 1

HCID 218337565'-Methoxycarbonyl-2'-methylbiphenyl-4-carboxylic acid収率 85%

試薬・触媒・溶媒 2

HCID 11979704Tetrakis(triphenylphosphine)palladium触媒
HCID 6228
Dimethylformamide
溶媒

反応条件

温度
100 °C

実験手順

A stirred solution of methyl 3-bromo-4-methylbenzoate (2.6 g, 0.011 mole) in dry DMF (20 ml) under argon was treated with 4-boronobenzoic acid (1.85 g, 0.011 mole) and tetrakis (triphenylphosphine) palladium(0) (400 mg), followed by triethylamine (4.68 ml, 0.046 mole). The mixture was heated at 100° C. for 18 hours, then concentrated in vacuo. The residue was treated with ethyl acetate and extracted with 10% NaHCO3 solution. The basic extract was acidified with dil. HCl and extracted with ethyl acetate. The extract was dried (Na2SO4) and concentrated in vacuo to afford the title compound as a light orange solid (2.12 g, 85%).

後処理

  1. concentrationconcentrated in vacuo
  2. additionThe residue was treated with ethyl acetate
  3. extractionextracted with 10% NaHCO3 solution
  4. extractionThe basic extract
  5. extractionextracted with ethyl acetate
  6. dry with materialThe extract was dried (Na2SO4)
  7. concentrationconcentrated in vacuo

出典と根拠

ORDレコード
ord-4c381ef49be94e3ab0565b01df8e6d7d
出典データセット
uspto-grants-1999_10
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US05972951

反応ノート

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