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

HRID 1175296ノート

反応式

HRID 1175296 の反応式
[Br:1][C:2]1[CH:7]=[C:6]([CH2:8][C:9]2[CH:14]=[CH:13][C:12]([CH2:15][CH3:16])=[CH:11][CH:10]=2)[C:5]([Cl:17])=[CH:4][C:3]=1[CH2:18][OH:19].[H-].[Na+].[CH2:22](Br)[CH:23]=[CH2:24]>CN(C=O)C.CCCC[N+](CCCC)(CCCC)CCCC.[I-]>[CH2:24]([O:19][CH2:18][C:3]1[CH:4]=[C:5]([Cl:17])[C:6]([CH2:8][C:9]2[CH:14]=[CH:13][C:12]([CH2:15][CH3:16])=[CH:11][CH:10]=2)=[CH:7][C:2]=1[Br:1])[CH:23]=[CH2:22]

参加物

6

反応物 3

HCID 7841Allyl bromideHCID 24758Sodium hydrideHCID 59467877(2-Bromo-5-chloro-4-(4-ethylbenzyl)phenyl)methanol

生成物 1

HCID 595576981-(Allyloxymethyl)-2-bromo-5-chloro-4-(4-ethylbenzyl)benzene収率 84.8%

試薬・触媒・溶媒 2

HCID 67553Tetrabutylammonium Iodide触媒HCID 6228Dimethylformamide溶媒2 回

反応条件

温度
-10 °C

実験手順

To a solution of (2-bromo-5-chloro-4-(4-ethylbenzyl)phenyl)methanol (3.4 g, 10 mmol) in DMF (50 mL) was added NaH (0.8 g, 20 mmol, 60% in miner oil) in portions at −5° C. After being stirred for 1 h at the same temperature, the reaction mixture was cooled to −10° C., TBAI (0.37 g, 1 mmol) and a solution of allyl bromide (1.45 g, 12 mmol) in DMF (10 mL) was added. The reaction mixture was stirred for another 1 h prior to quenching by ice water and extracted 3× with EtOAc. The combined organic layers were washed with brine and then dried over Na2SO4. Concentration gave the crude product, which was purified by silica column chromatography (elution with PE:EtOAc=10:1) to afford the title compound (3.22 g, yield 84.8%).

後処理

  1. stirringThe reaction mixture was stirred for another 1 h
  2. customto quenching by ice water
  3. extractionextracted 3× with EtOAc
  4. washThe combined organic layers were washed with brine
  5. dry with materialdried over Na2SO4
  6. concentrationConcentration
  7. customgave the crude product, which
  8. customwas purified by silica column chromatography (elution with PE:EtOAc=10:1)

出典と根拠

ORDレコード
ord-8b01a15909f149b8970b8d65b2ab05a1
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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