Fluorene → 2-Bromo-9H-fluorene

HRID 1268488Notes

Reaction equation

HRID 1268488 reaction equation
[CH:1]1[C:13]2[CH2:12][C:11]3[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=3)[C:5]=2[CH:4]=[CH:3][CH:2]=1.[Br:14]N1C(=O)CCC1=O>C1(=O)OC(C)CO1>[Br:14][C:9]1[CH:8]=[CH:7][C:6]2[C:5]3[C:13](=[CH:1][CH:2]=[CH:3][CH:4]=3)[CH2:12][C:11]=2[CH:10]=1

Participants

4

Reactant 2

HCID 6853FluoreneHCID 67184N-bromobutanimide

Product 1

HCID 143362-Bromo-9H-fluoreneYield 95%

Reagents, catalysts & solvents 1

HCID 7924Propylene CarbonateSolvent

Procedure

To a solution of fluorene (16.6 g, 0.1 mol), in propylene carbonate (125 mL), at 60° C., N-bromo succinimide (17.8 g, 0.1 mol) was added in one portion, and the mixture was allowed to cool over a period of 1 hour. The solids separated on dilution with water (2 L), were collected, dissolved in toluene (250 mL), and the toluene solution was washed with water. The solids left after concentration were recrystallized from ethanol-water, 23.3 g (95% yield), m.p. 95.6-101.3° C. Mass Spec: m/z 322, 324, 326 (M+ dibromo), 244,246 (M+).

Workup

  1. temperatureto cool over a period of 1 hour
  2. customThe solids separated on dilution with water (2 L)
  3. customwere collected
  4. dissolutiondissolved in toluene (250 mL)
  5. washthe toluene solution was washed with water
  6. waitThe solids left
  7. concentrationafter concentration
  8. customwere recrystallized from ethanol-water, 23.3 g (95% yield), m.p. 95.6-101.3° C

Sources & evidence

ORD record
ord-c43c11f7b1454abe8414ebdd456effab
Source dataset
uspto-grants-2003_04
Patent number
US06555682B1

Reaction notes

Loading…