Triphenylphosphine → 1-{[(2-Bromoethyl)oxy]methyl}-4-(1,1-dimethylethyl)benzene

HRID 1875663노트

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HRID 1875663 반응식
[Br:1]N1C(=O)CCC1=O.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[CH3:28][C:29]([C:32]1[CH:37]=[CH:36][C:35]([CH2:38][O:39][CH2:40][CH2:41]O)=[CH:34][CH:33]=1)([CH3:31])[CH3:30]>C(Cl)Cl.[Al]>[Br:1][CH2:41][CH2:40][O:39][CH2:38][C:35]1[CH:36]=[CH:37][C:32]([C:29]([CH3:31])([CH3:30])[CH3:28])=[CH:33][CH:34]=1

참가 물질

6

반응물 3

HCID 11776TriphenylphosphineHCID 67184N-bromobutanimideHCID 104885912-({[4-(1,1-Dimethylethyl)phenyl]methyl}oxy)ethanol

생성물 1

HCID 136543781-{[(2-Bromoethyl)oxy]methyl}-4-(1,1-dimethylethyl)benzene수율 12%

시약·촉매·용매 2

HCID 6344Dichloromethane용매4회HCID 5359268Aluminum용매

실험 절차

A solution of N-bromosuccinimide (272 mg, 1.53 mmol) in DCM (2.5 mL) was added to resin-bound triphenylphosphine (510 mg, 1.53 mEquiv, Fluka) in DCM (2.5 mL), and the reaction was stirred at rt for 10 min. A solution of 2-({[4-(1,1-dimethylethyl)phenyl]methyl}oxy)ethanol (160 mg, 0.768 mmol) in DCM (1.5 mL) was added to the reaction, and the residual alcohol was transferred with additional DCM (1.5 mL). The reaction vial was capped, wrapped in aluminum foil, and stirred at rt for 20 h. The reaction was filtered through a SPE cartridge (5 g silica) eluting with the following 10 mL fractions: DCM (fraction 1), 30% EtOAc/hexanes (fraction 2), and 50% EtOAc/hexanes (fraction 3) to give the title compound (25 mg, 12%). The product was characterized by 1H NMR (400 MHz) in CDCl3.

후처리

  1. customThe reaction vial was capped
  2. stirringstirred at rt for 20 h
  3. filtrationThe reaction was filtered through a SPE cartridge (5 g silica)
  4. washeluting with the following 10 mL fractions

출처 및 근거

ORD 기록
ord-995770c1a637475189d090889b75f588
출처 데이터셋
uspto-grants-2012_11
특허 번호
US08309572B2

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