ホームMCPワークベンチSkills
ホームワークベンチ通知マイページ
llms.txt · MCPガイドプライバシーポリシー · 利用規約 · サポートv1.8.0
  1. ホーム
  2. /反応

Sodium Carbonate → 2-Cyclopropyl-4'-fluoro-5-methoxybiphenyl-4-carbaldehyde

HRID 531049
ノート
印刷プレビュー

反応式

HRID 531049 の反応式
Br[C:2]1[CH:7]=[C:6]([CH:8]=[O:9])[C:5]([O:10][CH3:11])=[CH:4][C:3]=1[C:12]1[CH:17]=[CH:16][C:15]([F:18])=[CH:14][CH:13]=1.[CH:19]1(B(O)O)[CH2:21][CH2:20]1.C1(P(C2CCCCC2)C2C=CC=CC=2C2C(OC)=CC=CC=2OC)CCCCC1.C(=O)([O-])[O-].[Na+].[Na+]>C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd].O.C1(C)C=CC=CC=1>[CH:19]1([C:2]2[CH:7]=[C:6]([CH:8]=[O:9])[C:5]([O:10][CH3:11])=[CH:4][C:3]=2[C:12]2[CH:17]=[CH:16][C:15]([F:18])=[CH:14][CH:13]=2)[CH2:21][CH2:20]1
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

8

反応物 4

HCID 10340Sodium CarbonateHCID 2760897Cyclopropylboronic acidHCID 112698722-Dicyclohexylphosphino-2',6'-dimethoxybiphenylHCID 904235612-Bromo-4'-fluoro-5-methoxybiphenyl-4-carbaldehyde

生成物 1

HCID 904228222-Cyclopropyl-4'-fluoro-5-methoxybiphenyl-4-carbaldehyde収率 53.9%

試薬・触媒・溶媒 3

HCID 9811564
Bis(dibenzylideneacetone)palladium
触媒
HCID 962Water溶媒
HCID 1140Toluene溶媒

反応条件

温度
100 °C

実験手順

2-Bromo-4′-fluoro-5-methoxybiphenyl-4-carbaldehyde (20.6 g), cyclopropylboronic acid (10.3 g), dicyclohexyl(2′,6′-dimethoxybiphenyl-2-yl)phosphine (4.10 g), tris(dibenzylideneacetone)dipalladium(0) (4.27 g), and a 2 M aqueous sodium carbonate solution (100 mL) were added to toluene (250 mL) in an argon atmosphere, and the mixture was stirred at 100° C. for 2 hours. The reaction mixture was allowed to cool to room temperature and poured to water, followed by extraction with ethyl acetate. The obtained organic layer was washed with saturated saline and dried over anhydrous magnesium sulfate, and then, the solvent was distilled off under reduced pressure. The obtained residue was passed through a short silica gel column (hexane/ethyl acetate), and then, the filtrate was concentrated. The residue was crystallized from a mixed solution of ethanol (50 mL) and water (10 mL), and the obtained crystals were washed with ethanol (85 mL) to obtain the title compound (9.70 g).

後処理

  1. temperatureto cool to room temperature
  2. extractionfollowed by extraction with ethyl acetate
  3. washThe obtained organic layer was washed with saturated saline
  4. dry with materialdried over anhydrous magnesium sulfate
  5. distillationthe solvent was distilled off under reduced pressure
  6. concentrationthe filtrate was concentrated
  7. customThe residue was crystallized from a mixed solution of ethanol (50 mL) and water (10 mL)
  8. washthe obtained crystals were washed with ethanol (85 mL)

出典と根拠

ORDレコード
ord-01cbbd1ea6f3462ebf5ee84cf76a9f36
出典データセット
uspto-grants-2016_05
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US09353108B2

反応ノート

読み込み中…

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