Acetic Acid → HCID 89225180、化合物

HRID 2274530ノート

反応式

HRID 2274530 の反応式
[F:1][C:2]([F:16])([O:6][C:7]1[CH:8]=[C:9]([C:13](=[O:15])[CH3:14])[CH:10]=[CH:11][CH:12]=1)[CH:3]([F:5])[F:4].C(O)(=O)C.[Br:21]Br>C(OCC)C.C(Cl)Cl>[Br:21][CH2:14][C:13]([C:9]1[CH:10]=[CH:11][CH:12]=[C:7]([O:6][C:2]([F:16])([F:1])[CH:3]([F:4])[F:5])[CH:8]=1)=[O:15]

参加物

6

反応物 3

HCID 176Acetic AcidHCID 24408BromineHCID 716505571-[3-(1,1,2,2-Tetrafluoroethoxy)phenyl]ethanone

生成物 1

HCID 89225180HCID 89225180、化合物収率 61.5%

試薬・触媒・溶媒 2

HCID 3283Diethyl Ether溶媒HCID 6344Dichloromethane溶媒

反応条件

温度
25 °C

実験手順

1-[3-(1,1,2,2-tetrafluoroethoxy)phenyl]ethanone (6.1 g, 25.8 mmol) was dissolved in diethyl ether (36.9 mL), and acetic acid (44.4 mL, 775 mmol) was added, followed by bromine (1.397 mL, 27.1 mmol). The reaction was stirred at 25° C. for 3 hours, then was diluted with DCM and extracted with saturated sodium bicarbonate solution. The combined organic layers were dried with anhydrous MgSO4, filtered, and concentrated. The crude product was purified on a silica gel column with a 340 g cartridge, using a 10% EtOAc/Hexanes isocratic mobile phase. 2-Bromo-1-[3-(1,1,2,2-tetrafluoroethoxy)phenyl]ethanone (5 g, 15.87 mmol) was obtained. 1H NMR (400 MHz, CDCl3) 84.45 (s, 2H), 5.96 (t, J=53, 2.7 Hz, 1H), 7.47 (d, J=8.2 Hz, 1H), 7.55 (t, J=7.9 Hz, 1H), 7.83 (s, 1H), 7.91 (d, J=7.7 Hz, 1H).

後処理

  1. extractionextracted with saturated sodium bicarbonate solution
  2. dry with materialThe combined organic layers were dried with anhydrous MgSO4
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customThe crude product was purified on a silica gel column with a 340 g cartridge

出典と根拠

ORDレコード
ord-2aebbea1826f4cf1b59e35776231b542
出典データセット
uspto-grants-2015_09
特許番号
US09126976B2

反応ノート

読み込み中…