Bromine → N-(8-Bromobenzo[1,4]dioxan-5-yl)-acetamide

HRID 1487201ノート

反応式

HRID 1487201 の反応式
[O:1]1[CH2:6][CH2:5][O:4][C:3]2[C:7]([NH:11][C:12](=[O:14])[CH3:13])=[CH:8][CH:9]=[CH:10][C:2]1=2.[Br:15]Br>C(Cl)(Cl)Cl>[Br:15][C:10]1[C:2]2[O:1][CH2:6][CH2:5][O:4][C:3]=2[C:7]([NH:11][C:12](=[O:14])[CH3:13])=[CH:8][CH:9]=1

参加物

4

反応物 2

HCID 24408BromineHCID 658593N-(2,3-dihydro-1,4-benzodioxin-5-yl)acetamide

生成物 1

HCID 23269228N-(8-Bromobenzo[1,4]dioxan-5-yl)-acetamide収率 64.5%

試薬・触媒・溶媒 1

HCID 6212Chloroform溶媒2 回

反応条件

温度
0 °C

実験手順

To a solution of N-(2,3-dihydrobenzo[b][1,4]dioxin-5-yl)acetamide (5.5 g, 28.5 mmol) in chloroform (20 mL) cooled at −20° C. was slowly added a solution of bromine (1.6 mL, 30 mmol) in chloroform (5 mL) so that the reaction temperature was maintained below −10° C. The reaction was stirred at 0° C. for 10 minutes, and then quenched immediately with water. The mixture was extracted with dichloromethane; the combined extracts were washed with saturated sodium bicarbonate and brine, dried over anhydrous sodium sulfate, filtered and concentrated under reduced pressure. The residue was subjected to silica gel chromatography (dichloromethane) to afford the product N-(8-bromo-2,3-dihydrobenzo[b][1,4]dioxin-5-yl)acetamide (5 g, yield 64%). 1H NMR (400 MHz, CDCl3) δ ppm 9.23 (s, 1H), 7.46-7.48 (d, 1H, J=8.8 Hz), 7.04-7.06 (d, 1H, J=9.2 Hz), 4.32-4.40 (m, 4H), 2.07 (s, 3H).

後処理

  1. temperaturewas maintained below −10° C
  2. customquenched immediately with water
  3. extractionThe mixture was extracted with dichloromethane
  4. washthe combined extracts were washed with saturated sodium bicarbonate and brine
  5. dry with materialdried over anhydrous sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure

出典と根拠

ORDレコード
ord-998f2ee94ffd4bcf99e63d2f61b440e5
出典データセット
uspto-grants-2016_08
特許番号
US09428508B2

反応ノート

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