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

HRID 633724
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HRID 633724 반응식
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
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참가 물질

6

반응물 3

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

생성물 1

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

시약·촉매·용매 2

HCID 3283Diethyl Ether용매HCID 6344Dichloromethane
용매

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온도
0 °C

실험 절차

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:

후처리

  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)

출처 및 근거

ORD 기록
ord-9e3ba070fc454b869b3c9942eca52cf1
출처 데이터셋
uspto-grants-2016_04
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US09321790B2

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