N-bromobutanimide → 2-Bromofluorenone

HRID 1994179Notes

Reaction equation

HRID 1994179 reaction equation
[C:1]1(=[O:14])[C:13]2[C:5]([C:6]3[C:11]([CH:12]=2)=[CH:10][CH:9]=[CH:8][CH:7]=3)=[CH:4][CH:3]=[CH:2]1.[Br:15]N1C(=O)CCC1=O>CS(O)(=O)=O>[Br:15][C:2]1[C:1](=[O:14])[C:13]2[C:5](=[CH:4][CH:3]=1)[C:6]1[C:11](=[CH:10][CH:9]=[CH:8][CH:7]=1)[CH:12]=2

Participants

4

Reactant 2

HCID 67184N-bromobutanimide3×HCID 22281833Fluoreneone

Product 1

HCID 668106542-Bromofluorenone

Reagents, catalysts & solvents 1

HCID 6395Methanesulfonic AcidSolvent

Procedure

Fluorenone (41 grams (g); 0.228 mol) was dissolved in 225 milliliters (ml) of methanesulfonic acid and treated portion wise at room temperature with solid N-bromosuccinimide (NBS) (38.55 g; 0.217 mol). The mixture became dark and warm, and the temperature was maintained below 60° C. by controlling the rate of NBS addition. Upon completion of the NBS addition, the mixture was allowed to cool to room temperature and was poured into 1 liter of ice water. The yellow solid that separated was collected by filtration, washed with copious quantities of water, air dried, and then recrystallized from about 1.5 liters of ethanol. The yield was 40 g (71%) and the product contained 5-10% of 2,7-dibromofluorenone as indicated by LC analysis. A small sample was purified by column chromatography, but in general the contaminated material was carried on in subsequent steps.

Workup

  1. temperaturewarm
  2. temperaturethe temperature was maintained below 60° C.
  3. customThe yellow solid that separated
  4. filtrationwas collected by filtration
  5. washwashed with copious quantities of water, air
  6. customdried
  7. customrecrystallized from about 1.5 liters of ethanol
  8. customA small sample was purified by column chromatography

Sources & evidence

ORD record
ord-234505d9deaf498c9a03fa87a77bc0ee
Source dataset
uspto-grants-2010_01
Patent number
US07652126B2

Reaction notes

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