N-bromobutanimide → HCID 68813816, compound

HRID 2105092Notes

Reaction equation

HRID 2105092 reaction equation
[C:1]1([C:7]2([C:22]3[CH:27]=[CH:26][C:25]([CH3:28])=[CH:24][CH:23]=3)[C:19]3[CH:18]=[C:17]([Br:20])[CH:16]=[CH:15][C:14]=3[C:13]3[C:8]2=[CH:9][C:10]([Br:21])=[CH:11][CH:12]=3)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C1C(=O)N([Br:36])C(=O)C1>C(Cl)(Cl)(Cl)Cl>[C:1]1([C:7]2([C:22]3[CH:23]=[CH:24][C:25]([CH2:28][Br:36])=[CH:26][CH:27]=3)[C:8]3[CH:9]=[C:10]([Br:21])[CH:11]=[CH:12][C:13]=3[C:14]3[C:19]2=[CH:18][C:17]([Br:20])=[CH:16][CH:15]=3)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

4

Reactant 2

HCID 67184N-bromobutanimideHCID 58174915HCID 58174915, compound

Product 1

HCID 68813816HCID 68813816, compoundYield 89.8%

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Procedure

Into a flask, 9-phenyl-9-(4-methylphenyl)-2,7-dibromofluorene (0.90 g, 1.84 mmol), NBS (0.33 g, 1.84 mmol), BPO (0.044 g, 0.184 mmol) and CCl4 (10 ml) were added and reacted under reflux for 2 hr. Then, the reaction system was cooled and filtered. After removing the filtrate, a gray solid of 9-phenyl-9-(4-bromomethylphenyl)-2,7-dibromofluorene (0.94 g) was obtained as a pure intermediate product (yield, 90%). 1HNMR (300 MHz, CDCl3): δ 7.51-7.48 (m, 6H), 7.26-7.00 (M, 9H), 4.46 (s, 2H).

Workup

  1. customreacted
  2. temperatureunder reflux for 2 hr
  3. temperatureThen, the reaction system was cooled
  4. filtrationfiltered
  5. customAfter removing the filtrate

Sources & evidence

ORD record
ord-ac75054404e74bf1a67f4adb5f4fc2b4
Source dataset
uspto-grants-2009_08
Patent number
US07579091B2

Reaction notes

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