Acetic Acid → HCID 89225180, 화합물

HRID 2274530노트

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HRID 2274530 반응식
[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]

참가 물질

6

반응물 3

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

생성물 1

HCID 89225180HCID 89225180, 화합물수율 61.5%

시약·촉매·용매 2

HCID 3283Diethyl Ether용매HCID 6344Dichloromethane용매

반응 조건

온도
25 °C

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-2aebbea1826f4cf1b59e35776231b542
출처 데이터셋
uspto-grants-2015_09
특허 번호
US09126976B2

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