2-Fluoroethanol → 1-Bromo-3-(2-fluoroethoxymethyl)benzene

HRID 30583

반응식

HRID 30583 반응식
[H-].[Na+].[F:3][CH2:4][CH2:5][OH:6].[Br:7][C:8]1[CH:9]=[C:10]([CH:13]=[CH:14][CH:15]=1)[CH2:11]Br.[Cl-].[NH4+]>C1COCC1>[Br:7][C:8]1[CH:15]=[CH:14][CH:13]=[C:10]([CH2:11][O:6][CH2:5][CH2:4][F:3])[CH:9]=1

참가 물질

6

반응물 4

HCID 97372-FluoroethanolHCID 24758Sodium hydrideHCID 25517Ammonium ChlorideHCID 699793-Bromobenzyl bromide

생성물 1

HCID 150587701-Bromo-3-(2-fluoroethoxymethyl)benzene수율 58%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매2회

실험 절차

A mixture of sodium hydride [60% in oil] (343, mg, 8.6 mmol) and THF at −5° C. was treated via a syringe with a solution of 2-fluoroethanol in THF over a 1 min. period, stirred for 2 min., warmed to room temperature, stirred for 15 min. at room temperature, treated with 3-bromobenzylbromide (2.5 g, 11.7 mmol), stirred for 1 h, poured into saturated ammonium chloride and extracted with ether. The extracts were combined, washed sequentially with water and brine, dried over magnesium sulfate and concentrated under reduced pressure. The residue was purified by flash chromatography on silica gel, 20:1 hexane/ ethyl acetate as eluent, to afford 1-bromo-3-(2-fluoroethoxymethyl)benzene as a yellow oil, 1 g (58% yield), 1H NMR (DMSO-d6) δ 3.6 (dxt, 2H); 4.5 (dxt, 2H); 4.4 (s, 2 H); 7.3 (m, 2H); 7.5 (m, 2H); MS [(+)ESI] m/z 219 [M−H]+.

후처리

  1. stirringstirred for 15 min. at room temperature
  2. stirringstirred for 1 h
  3. extractionextracted with ether
  4. washwashed sequentially with water and brine
  5. dry with materialdried over magnesium sulfate
  6. concentrationconcentrated under reduced pressure
  7. customThe residue was purified by flash chromatography on silica gel, 20:1 hexane/ ethyl acetate as eluent

출처 및 근거

ORD 기록
ord-158d176688544e6aa2e5b276473b5061
출처 데이터셋
uspto-grants-2008_09
특허 번호
US07423158B2

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