2-Phenylethanol → 1-Iodo-3-(phenethoxymethyl)benzene

HRID 2095334ノート

反応式

HRID 2095334 の反応式
[C:1]1([CH2:7][CH2:8][OH:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[H-].[Na+].[I:12][C:13]1[CH:14]=[C:15]([CH:18]=[CH:19][CH:20]=1)[CH2:16]Br>O1CCCC1.[N+](CCCC)(CCCC)(CCCC)CCCC.[Br-]>[I:12][C:13]1[CH:20]=[CH:19][CH:18]=[C:15]([CH2:16][O:9][CH2:8][CH2:7][C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)[CH:14]=1

参加物

6

反応物 3

HCID 60542-PhenylethanolHCID 24758Sodium hydrideHCID 27593613-Iodobenzyl bromide

生成物 1

HCID 593714071-Iodo-3-(phenethoxymethyl)benzene収率 99%

試薬・触媒・溶媒 2

HCID 74236Tetrabutylammonium Bromide触媒HCID 8028Tetrahydrofuran溶媒

反応条件

温度
25 °C

実験手順

Into a 100 mL round-bottom flask was placed under N2 a solution of 2-phenylethanol (110 mg, 0.90 mmol) in tetrahydrofuran (10 mL). Sodium hydride (26 mg, 1.08 mmol, 1.2 equiv.) was added with ice cooling. The mixture was stirred for 2 h at 25° C., then 3-iodobenzyl bromide (320 mg, 1.08 mmol, 1.2 equiv.) and n-Bu4NBr (30 mg, 0.09 mmol, 0.10 equiv.) were added. The resulting solution was stirred for 20 h at 25° C. The reaction progress was monitored by TLC (SiO2, EtOAc/petroleum ether 1:5). The reaction was quenched by the addition of saturated aqueous NH4Cl solution. The resulting solution was extracted with EtOAc, and the organic layers were combined, dried over Na2SO4, and concentrated under vacuum. The residue was chromatographed on silica gel with EtOAc/petroleum ether 1:20 to obtain 300 mg (99%) of 1-iodo-3-(phenethoxymethyl)benzene as a yellow oil.

後処理

  1. customInto a 100 mL round-bottom flask was placed under N2
  2. stirringThe resulting solution was stirred for 20 h at 25° C
  3. customThe reaction was quenched by the addition of saturated aqueous NH4Cl solution
  4. extractionThe resulting solution was extracted with EtOAc
  5. dry with materialdried over Na2SO4
  6. concentrationconcentrated under vacuum
  7. customThe residue was chromatographed on silica gel with EtOAc/petroleum ether 1:20

出典と根拠

ORDレコード
ord-8afacb9fdaab4e28a0f430e930806244
出典データセット
uspto-grants-2013_05
特許番号
US08445684B2

反応ノート

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