2-Bromoethanol → 2-(3-Nitrophenoxy)ethanol

HRID 548237노트

반응식

HRID 548237 반응식
[N+:1]([C:4]1[CH:5]=[C:6]([OH:10])[CH:7]=[CH:8][CH:9]=1)([O-:3])=[O:2].[OH-].[Na+].Br[CH2:14][CH2:15][OH:16]>CN(C=O)C>[N+:1]([C:4]1[CH:5]=[C:6]([CH:7]=[CH:8][CH:9]=1)[O:10][CH2:14][CH2:15][OH:16])([O-:3])=[O:2]

참가 물질

5

반응물 3

HCID 108982-BromoethanolHCID 111373-NitrophenolHCID 14798Sodium Hydroxide

생성물 1

HCID 46689272-(3-Nitrophenoxy)ethanol

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

반응 조건

온도
60 °C

실험 절차

To a solution of 3-nitrophenol (10 g, 71.9 mmol) in DMF (40 ml) was added NaOH pellets (3.16 g, 79.1 mmol) and 2-bromoethanol (5.6 ml, 79.1 mmol). The reaction mixture was heated at 60° C. for 18 h. LCMS indicated 65% conversion to the required product. The reaction mixture was diluted with water (10 ml) and was slowly neutralised with 2M HCl. The reaction mixture was extracted with EtOAc (50 ml) and washed with water (50 ml). The EtOAc layer dried (Na2SO4), filtered and evaporated to dryness. Flash column chromatography purification eluting with 30% EtOAc/heptane gave the required product (8.2 g, 62% yield). LCMS purity 100%, m/z 184 [M+H]+.

출처 및 근거

ORD 기록
ord-5ddeb0707199475481d824fc2d048575
출처 데이터셋
uspto-grants-2011_05
특허 번호
US07939666B2

반응 노트

불러오는 중…