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Triphenylphosphine → tert-Butyl (4-(2-bromoethyl)phenyl)carbamate

HRID 633724
ノート
印刷プレビュー

反応式

HRID 633724 の反応式
C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.O[CH2:21][CH2:22][C:23]1[CH:28]=[CH:27][C:26]([NH:29][C:30](=[O:36])[O:31][C:32]([CH3:35])([CH3:34])[CH3:33])=[CH:25][CH:24]=1.[Br:37]N1C(=O)CCC1=O>ClCCl.CCOCC>[Br:37][CH2:21][CH2:22][C:23]1[CH:28]=[CH:27][C:26]([NH:29][C:30](=[O:36])[O:31][C:32]([CH3:35])([CH3:34])[CH3:33])=[CH:25][CH:24]=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

6

反応物 3

HCID 11776TriphenylphosphineHCID 67184N-bromobutanimideHCID 11413715N-Boc-2-(4-aminophenyl)ethanol

生成物 1

HCID 24800457tert-Butyl (4-(2-bromoethyl)phenyl)carbamate収率 69.5%

試薬・触媒・溶媒 2

HCID 3283Diethyl Ether溶媒HCID 6344Dichloromethane
溶媒

反応条件

温度
0 °C

実験手順

8.68 g (33.08 mmol) of triphenylphosphine are added, under an argon atmosphere, to a solution of 7.85 g (33.08 mmol) of tert-butyl [4-(2-hydroxyethyl)phenyl]carbamate in 85 mL of dichloromethane. The mixture is cooled to 0° C. and 5.95 g (33.08 mmol) of N-bromosuccinimide are added portionwise over 25 minutes. Stirring is continued for 3 hours at 0° C. The solvent is then evaporated off, the oil obtained is taken up in ether and the precipitate formed is filtered off and discarded. The filtrate is evaporated and the residue is purified by chromatography on silica gel (eluent: 10/90 EtOAc/heptane) to give 6.90 g of tert-butyl [4-(2-bromoethyl)phenyl]carbamate, the characteristics of which are as follows:

後処理

  1. customThe solvent is then evaporated off
  2. customthe oil obtained
  3. customthe precipitate formed
  4. filtrationis filtered off
  5. customThe filtrate is evaporated
  6. customthe residue is purified by chromatography on silica gel (eluent: 10/90 EtOAc/heptane)

出典と根拠

ORDレコード
ord-9e3ba070fc454b869b3c9942eca52cf1
出典データセット
uspto-grants-2016_04
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US09321790B2

反応ノート

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