Potassium Carbonate → (1-((4-Iodo-2-nitrophenoxy)methyl)cyclopropyl)methanol

HRID 575463

반응식

HRID 575463 반응식
F[C:2]1[CH:7]=[CH:6][C:5]([I:8])=[CH:4][C:3]=1[N+:9]([O-:11])=[O:10].[OH:12][CH2:13][C:14]1([CH2:17][OH:18])[CH2:16][CH2:15]1.C([O-])([O-])=O.[K+].[K+]>CN(C=O)C>[I:8][C:5]1[CH:6]=[CH:7][C:2]([O:12][CH2:13][C:14]2([CH2:17][OH:18])[CH2:16][CH2:15]2)=[C:3]([N+:9]([O-:11])=[O:10])[CH:4]=1

참가 물질

5

반응물 3

HCID 11430Potassium CarbonateHCID 41014371,1-Bis(hydroxymethyl)cyclopropaneHCID 145905821-Fluoro-4-iodo-2-nitrobenzene

생성물 1

HCID 86693527(1-((4-Iodo-2-nitrophenoxy)methyl)cyclopropyl)methanol수율 71%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

반응 조건

온도
50 °C

실험 절차

A solution of 1-fluoro-4-iodo-2-nitrobenzene (2.50 g, 9.4 mmol) in DMF (30 mL) was treated with 1-(hydroxymethyl)cyclopropylmethanol (1.91 g, 19 mmol) and K2CO3 (2.6 g, 19 mmol) and the mixture was heated at 50° C. for 8 hours. TLC indicated complete consumption of the arylfluoride. The mixture was diluted with water and extracted with ethyl acetate. The combined organics were washed with brine, dried over sodium sulfate and concentrated by rotoevaporation. Purification by flash column chromatography (EtOAc in heptanes) gave the titled compound as a light yellow solid (2.31 g, 71% yield). 1H NMR (400 MHz, DMSO) δ 8.15 (d, J=2.2 Hz, 1H), 7.92 (dd, J=8.8, 2.2 Hz, 1H), 7.17 (d, J=8.9 Hz, 1H), 4.60 (t, J=5.6 Hz, 1H), 4.05 (s, 2H), 3.36 (d, J=5.6 Hz, 2H), 0.50 (s, 4H).

후처리

  1. customconsumption of the arylfluoride
  2. additionThe mixture was diluted with water
  3. extractionextracted with ethyl acetate
  4. washThe combined organics were washed with brine
  5. dry with materialdried over sodium sulfate
  6. concentrationconcentrated by rotoevaporation
  7. customPurification by flash column chromatography (EtOAc in heptanes)

출처 및 근거

ORD 기록
ord-af1aafb3e9064f4bac3bdba56441a578
출처 데이터셋
uspto-grants-2015_05
특허 번호
US09034866B2

연결된 노트

불러오는 중…