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Dimethylformamide → 4-(4-Cyanonaphthalene-2-yl)benzoic acid methyl ester

HRID 2383344
ノート
印刷プレビュー

反応式

HRID 2383344 の反応式
[CH3:1][O:2][C:3]([C:5]1[CH:10]=[CH:9][C:8](B(O)O)=[CH:7][CH:6]=1)=[O:4].Br[C:15]1[CH:16]=[C:17]([C:25]#[N:26])[C:18]2[C:23]([CH:24]=1)=[CH:22][CH:21]=[CH:20][CH:19]=2.C(=O)([O-])[O-].[Cs+].[Cs+].CN(C)C=O>C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.O>[CH3:1][O:2][C:3](=[O:4])[C:5]1[CH:10]=[CH:9][C:8]([C:15]2[CH:16]=[C:17]([C:25]#[N:26])[C:18]3[C:23](=[CH:22][CH:21]=[CH:20][CH:19]=3)[CH:24]=2)=[CH:7][CH:6]=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

7

反応物 4

HCID 6228DimethylformamideHCID 10796Cesium carbonateHCID 27343694-Methoxycarbonylphenylboronic acidHCID 534856703-Bromonaphthalene-1-carbonitrile

生成物 1

HCID 673093094-(4-Cyanonaphthalene-2-yl)benzoic acid methyl ester収率 40.4%

試薬・触媒・溶媒 2

HCID 178418397
HCID 178418397、化合物
触媒
HCID 962Water溶媒2 回

反応条件

温度
150 °C

実験手順

4-Methoxycarbonylphenylboronic acid (0.039 g), 3-bromonaphthalene-1-carbonitrile (0.05 g), tetrakis(triphenylphosphine)palladium (0.012 g) and cesium carbonate (0.11 g) were suspended in a mixed solvent of N,N-dimethylformamide (3 mL) and water (1 mL), and the resulting mixture was stirred at 150° C. for 40 minutes using microwave reactor (Biotage). The reaction mixture was poured into water, and the resulting mixture was extracted with ethyl acetate. The organic layer was concentrated under reduced pressure, and the residue was purified by column chromatography on silica gel (eluent: n-hexane/ethyl acetate=100/0-66/34) to give 4-(4-cyanonaphthalene-2-yl)benzoic acid methyl ester (0.025 g).

後処理

  1. extractionthe resulting mixture was extracted with ethyl acetate
  2. concentrationThe organic layer was concentrated under reduced pressure
  3. customthe residue was purified by column chromatography on silica gel (eluent: n-hexane/ethyl acetate=100/0-66/34)

出典と根拠

ORDレコード
ord-0979bd66d23e46ae90f0ad02438dc44b
出典データセット
uspto-grants-2012_09
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08263622B2

反応ノート

読み込み中…

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