Allyl bromide → 1-(2-(Allyloxy)ethoxy)-2-bromo-5-chloro-4-(4-ethylbenzyl)benzene

HRID 1175319ノート

反応式

HRID 1175319 の反応式
[Br:1][C:2]1[CH:11]=[C:10]([CH2:12][C:13]2[CH:18]=[CH:17][C:16]([CH2:19][CH3:20])=[CH:15][CH:14]=2)[C:9]([Cl:21])=[CH:8][C:3]=1[O:4][CH2:5][CH2:6][OH:7].[H-].[Na+].[CH2:24](Br)[CH:25]=[CH2:26]>CN(C=O)C>[CH2:26]([O:7][CH2:6][CH2:5][O:4][C:3]1[CH:8]=[C:9]([Cl:21])[C:10]([CH2:12][C:13]2[CH:14]=[CH:15][C:16]([CH2:19][CH3:20])=[CH:17][CH:18]=2)=[CH:11][C:2]=1[Br:1])[CH:25]=[CH2:24]

参加物

5

反応物 3

HCID 7841Allyl bromideHCID 24758Sodium hydrideHCID 595577142-(2-Bromo-5-chloro-4-(4-ethylbenzyl)phenoxy)ethanol

生成物 1

HCID 595577091-(2-(Allyloxy)ethoxy)-2-bromo-5-chloro-4-(4-ethylbenzyl)benzene収率 85%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

To a solution of 2-(2-bromo-5-chloro-4-(4-ethylbenzyl)phenoxy)ethanol (AU) (1.85 g, 5 mmol) in anhydrous DMF (10 mL), NaH (0.36 g 15 mmol) was added in portions, and the mixture was stirred at room temperature for 2 hours. Then allyl bromide (1.82 g, 15 mmol) was added dropwise, and the mixture was heated to 45° C. overnight. The reaction was quenched with the saturated NH4Cl and the mixture was extracted with EtOAc, and then washed with water and brine. After drying with anhydrous Na2SO4, the organic portion was filtered and concentrated. The residue was purified by flash chromatography to give AV as an oil (1.74 g, yield 85%). 1H-NMR (CDCl3, 300 MHz) δ 7.31 (s, 1H), 7.13 (m, 4H), 6.94 (s, 1H), 5.94 (m, 1H), 5.26 (m, 2H), 4.14 (m, 4H), 3.96 (s, 2H), 3.84 (m, 2H), 2.64 (q, J=7.5 Hz, 2H), 1.22 (t, J=7.5 Hz, 3H).

後処理

  1. temperaturethe mixture was heated to 45° C. overnight
  2. customThe reaction was quenched with the saturated NH4Cl
  3. extractionthe mixture was extracted with EtOAc
  4. washwashed with water and brine
  5. dry with materialAfter drying with anhydrous Na2SO4
  6. filtrationthe organic portion was filtered
  7. concentrationconcentrated
  8. customThe residue was purified by flash chromatography

出典と根拠

ORDレコード
ord-be2cfe62a028479a99bf001549c84027
出典データセット
uspto-grants-2010_11
特許番号
US07838498B2

反応ノート

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