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

HRID 30583

反応式

HRID 30583 の反応式
[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

参加物

6

反応物 4

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

生成物 1

HCID 150587701-Bromo-3-(2-fluoroethoxymethyl)benzene収率 58%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒2 回

実験手順

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]+.

後処理

  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

出典と根拠

ORDレコード
ord-158d176688544e6aa2e5b276473b5061
出典データセット
uspto-grants-2008_09
特許番号
US07423158B2

関連ノート

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