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

HRID 553056ノート

反応式

HRID 553056 の反応式
[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

参加物

7

反応物 4

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

生成物 1

HCID 574398702-Bromo-7-iodo-9H-fluoren-9-one収率 80%

試薬・触媒・溶媒 2

HCID 1118Sulfuric Acid触媒HCID 176Acetic Acid溶媒

実験手順

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)+.

後処理

  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

出典と根拠

ORDレコード
ord-08a75e2a9784418f88ccab58ef3a7669
出典データセット
uspto-grants-2011_05
特許番号
US07951791B2

反応ノート

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