Acetic Acid → 2,7-Dibromo-9,9'-spirobi[fluorene]

HRID 2352749Notes

Reaction equation

HRID 2352749 reaction equation
[Br:1][C:2]1[C:3](=O)[C:4]2[C:12](=[CH:13][CH:14]=1)[C:11]1[C:6](=[CH:7][C:8]([Br:15])=[CH:9][CH:10]=1)[CH:5]=2.[C:17](O)(=O)[CH3:18]>CCOCC>[Br:1][C:2]1[CH:14]=[CH:13][C:12]2[C:11]3[C:6](=[CH:7][C:8]([Br:15])=[CH:9][CH:10]=3)[C:5]3([C:18]4[CH:17]=[CH:8][CH:7]=[CH:6][C:5]=4[C:4]4[C:3]3=[CH:2][CH:14]=[CH:13][CH:12]=4)[C:4]=2[CH:3]=1

Participants

4

Reactant 2

HCID 176Acetic AcidHCID 534201032,7Dibromofluorenone

Product 1

HCID 155447672,7-Dibromo-9,9'-spirobi[fluorene]Yield 60%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

According to a method similar to that of synthesis example 3, 2,7-dibromofluorenone (0.1 mol) and 2-biphenyl magnesium bromide are agitated in ether for 3 hr, followed by cooling to room temperature, further followed by slowly adding 50 ml of acetic acid. Ether is distilled away under reduced pressure, followed by adding thereto substantially 5 ml of HCl. Thereafter, the solution is refluxed for 1 hr, followed by filtering precipitate by suction, further followed by washing with water and recrystallizing with methanol. Thereby, 2,7-dibromo-9,9′-spirobifluorene is obtained (yield: 60%).

Workup

  1. distillationEther is distilled away under reduced pressure
  2. additionby adding
  3. temperatureThereafter, the solution is refluxed for 1 hr
  4. filtrationby filtering precipitate by suction
  5. washby washing with water
  6. customrecrystallizing with methanol

Sources & evidence

ORD record
ord-9c4abf5b81b6451b9188e9efe6fb1ae5
Source dataset
uspto-grants-2010_07
Patent number
US07749618B2

Reaction notes

Loading…