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

HRID 902989Notes

Reaction equation

HRID 902989 reaction equation
[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

Participants

7

Reactant 4

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

Product 1

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

Reagents, catalysts & solvents 2

HCID 1118Sulfuric AcidCatalystHCID 176Acetic AcidSolvent

Procedure

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 (DCl/NH3): m/z 384 (M+1)+, 386 (M+3)+.

Workup

  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

Sources & evidence

ORD record
ord-ab5b3a0a995643d8acf7c696ea835206
Source dataset
uspto-grants-2008_04
Patent number
US07365193B2

Reaction notes

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