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tert-Butyl 4'-(bromomethyl)biphenyl-2-carboxylate → N-[[2'-(t-butoxycarbonyl)biphenyl-4-yl]methyl]phthalimide

HRID 1046694
ノート
印刷プレビュー

反応式

HRID 1046694 の反応式
[C:1]([O:5][C:6]([C:8]1[C:9]([C:14]2[CH:19]=[CH:18][C:17]([CH2:20]Br)=[CH:16][CH:15]=2)=[CH:10][CH:11]=[CH:12][CH:13]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[C:22]1(=[O:32])[NH:26][C:25](=[O:27])[C:24]2=[CH:28][CH:29]=[CH:30][CH:31]=[C:23]12.[K]>CN(C=O)C>[C:1]([O:5][C:6]([C:8]1[C:9]([C:14]2[CH:19]=[CH:18][C:17]([CH2:20][N:26]3[C:22](=[O:32])[C:23]4[C:24](=[CH:28][CH:29]=[CH:30][CH:31]=4)[C:25]3=[O:27])=[CH:16][CH:15]=2)=[CH:10][CH:11]=[CH:12][CH:13]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2]
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

4

反応物 2

HCID 9906257tert-Butyl 4'-(bromomethyl)biphenyl-2-carboxylateHCID 24194345Phthalimide potassium salt

生成物 1

HCID 10024731N-[[2'-(t-butoxycarbonyl)biphenyl-4-yl]methyl]phthalimide

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

反応条件

温度
50 °C

実験手順

4′-Bromomethylbiphenyl-2-carboxylic acid t-butyl ester (4.0 g, 11.5 mmol) and potassium phthalimide were combined and dissolved in DMF (30 mL), and the mixture was heated at 50° C. for two days. The mixture was then cooled to room temperature and the reaction quenched with water (30 mL). The mixture was then extracted with EtOAc, and washed with a 10% aqueous lithium chloride solution. The organic layer was dried over MgSO4, filtered and concentrated to obtain intermediate (22a) (4.8 g). MS m/z: [M+H+] calcd for C26H23NO4, 414.5. found 414.3.

後処理

  1. temperatureThe mixture was then cooled to room temperature
  2. customthe reaction quenched with water (30 mL)
  3. extractionThe mixture was then extracted with EtOAc
  4. washwashed with a 10% aqueous lithium chloride solution
  5. dry with materialThe organic layer was dried over MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated

出典と根拠

ORDレコード
ord-9744d14e7db748a18fae956c28f21d34
出典データセット
uspto-grants-2013_10
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08569351B2

反応ノート

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