Bromine → 2-Bromo-7-iodo-9H-fluoren-9-one

HRID 553056노트

반응식

HRID 553056 반응식
[I:1][C:2]1[CH:14]=[CH:13][C:12]2[C:11]3[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=3)[C:5](=[O:15])[C:4]=2[CH:3]=1.C(O)(=O)C.C(O)(=O)C.IC1C=CC=CC=1.CC(OC(C)=O)=O.CC(O)=O.[Br:42]Br>S(=O)(=O)(O)O.C(O)(=O)C>[Br:42][C:8]1[CH:9]=[CH:10][C:11]2[C:12]3[C:4](=[CH:3][C:2]([I:1])=[CH:14][CH:13]=3)[C:5](=[O:15])[C:6]=2[CH:7]=1

참가 물질

7

반응물 4

HCID 24408BromineHCID 2486172-Iodo-9-fluorenoneHCID 12217721Iodo benzene diacetateHCID 21895370AcOH AcOAc

생성물 1

HCID 574398702-Bromo-7-iodo-9H-fluoren-9-one수율 80%

시약·촉매·용매 2

HCID 1118Sulfuric Acid촉매HCID 176Acetic Acid용매

실험 절차

A suspension of 2-iodofluoren-9-one (1.046 g, 3.42 mmol; Maybridge) and iodobenzene diacetate (1.21 g, 3.76 mmol; Aldrich) in 1:1 Ac2O—HOAc (10 mL) was treated with bromine (180 μL, 3.48 mmol; Aldrich) followed by 3 drops concentrated sulfuric acid. The mixture solidified, so it was diluted with acetic acid until it could be stirred. After 2 h, the reaction was quenched with aq. Na2S2O3, neutralized with K2CO3, and filtered. The solid filter cake was washed with water, dried, and recrystallized from hot EtOH to afford the title compound (1.05 g, 2.73 mmol; 80% yield): 1H NMR (300 MHz, CDCl3) δ ppm 7.97 (dd, J=2, 1 Hz, 1H), 7.84 (dd, J=8, 2 Hz, 1H), 7.75-7.79 (m, 1H), 7.63 (dd, J=8, 2 Hz, 1H), 7.39 (d, J=7 Hz, 1H), 7.24-7.31 (m, 1H); MS (DCI/NH3): m/z 384 (M+1)+, 386 (M+3)+.

후처리

  1. customthe reaction was quenched with aq. Na2S2O3
  2. filtrationfiltered
  3. filtrationThe solid filter cake
  4. washwas washed with water
  5. customdried
  6. customrecrystallized from hot EtOH

출처 및 근거

ORD 기록
ord-08a75e2a9784418f88ccab58ef3a7669
출처 데이터셋
uspto-grants-2011_05
특허 번호
US07951791B2

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