Triphenylphosphine → 1-(2-Bromo-ethoxymethyl)-4-chlorobenzene

HRID 533870노트

반응식

HRID 533870 반응식
[Br:1]N1C(=O)CCC1=O.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[Cl:28][C:29]1[CH:34]=[CH:33][C:32]([CH2:35][O:36][CH2:37][CH2:38]O)=[CH:31][CH:30]=1>C(Cl)Cl.[Al]>[Br:1][CH2:38][CH2:37][O:36][CH2:35][C:32]1[CH:33]=[CH:34][C:29]([Cl:28])=[CH:30][CH:31]=1

참가 물질

6

반응물 3

HCID 11776TriphenylphosphineHCID 67184N-bromobutanimideHCID 27637512-[(4-Chlorobenzyl)oxy]-1-ethanol

생성물 1

HCID 136543741-(2-Bromo-ethoxymethyl)-4-chlorobenzene수율 57%

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-chlorophenyl)methyl]oxy}ethanol (129 mg, 0.691 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 (98 mg, 57%). 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-da44829bc447435a83f4f386b9b9a026
출처 데이터셋
uspto-grants-2014_10
특허 번호
US08853404B2

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