Isopropyl iodide → Methyl 2-(4-bromophenyl)-3-methylbutanoate

HRID 1525240ノート

反応式

HRID 1525240 の反応式
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][C:9]([O:11][CH3:12])=[O:10])=[CH:4][CH:3]=1.[CH3:13][C:14]([O-])(C)[CH3:15].[K+].IC(C)C>CN(C=O)C>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([CH:8]([CH:14]([CH3:15])[CH3:13])[C:9]([O:11][CH3:12])=[O:10])=[CH:6][CH:7]=1

参加物

5

反応物 3

HCID 6362Isopropyl iodideHCID 316783Methyl 2-(4-bromophenyl)acetateHCID 23665647Potassium tert-butoxide

生成物 1

HCID 46855859Methyl 2-(4-bromophenyl)-3-methylbutanoate収率 48%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒2 回

反応条件

温度
0 °C

実験手順

To a solution of methyl 2-(4-bromophenyl)acetate, 13-a, (2.29 g, 10 mmol) in DMF (40 ml) was added dropwise a mixture of t-BuOK (1.12 g, 10 mmol) in DMF (20 mL) with stirring at 0° C. under a nitrogen atmosphere. After stirring at 0° C. for 30 min, 2-iodopropane (1.70 g, 10 mmol) was added dropwise. Then the resulting solution was stirred overnight and ice-water was added. The aqueous layer was extracted by EA. The combined organic layers were washed by brine, dried over Na2SO4 and concentrated. The crude product was purified by column chromatography to afford the title compound, 13-b, (1.3 g, 48%). 1H NMR (300 MHz, CDCl3) δ 0.70-0.72 (m, 3H), 1.02-1.04 (m, 3H), 2.27-2.32 (m, 1H), 3.10-3.14 (m, 1H), 3.65 (s, 3H), 7.19-7.24 (m, 2H), 7.42-7.45 (m, 2H). LC-MS: (M+H)+ 254, 256.

後処理

  1. stirringAfter stirring at 0° C. for 30 min
  2. stirringThen the resulting solution was stirred overnight
  3. extractionThe aqueous layer was extracted by EA
  4. washThe combined organic layers were washed by brine
  5. dry with materialdried over Na2SO4
  6. concentrationconcentrated
  7. customThe crude product was purified by column chromatography

出典と根拠

ORDレコード
ord-0892e3544df246b6b32406941df6b35d
出典データセット
uspto-grants-2015_07
特許番号
US09079930B2

反応ノート

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