Fluorene → 9-Bromofluorene

HRID 1608710Notes

Reaction equation

HRID 1608710 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>C(OOC(=O)C1C=CC=CC=1)(=O)C1C=CC=CC=1.C(Cl)(Cl)(Cl)Cl>[Br:14][CH:12]1[C:11]2[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=2[C:5]2[C:13]1=[CH:1][CH:2]=[CH:3][CH:4]=2

Participants

5

Reactant 2

HCID 6853FluoreneHCID 67184N-bromobutanimide

Product 1

HCID 160249-BromofluoreneYield 55%

Reagents, catalysts & solvents 2

HCID 7187Benzoyl PeroxideCatalystHCID 5943Carbon TetrachlorideSolvent

Procedure

A mixture of fluorene (MW 166, 0.36M, 59.76 g), N-bromosuccinimide (MW 178, 0.36M, 64.1 g), benzoyl peroxide (MW 242, 0.0036M, 0.87 g) and carbon tetrachloride (360 ml) was stirred at reflux for 3 hours. After cooling to room temperature and screening, the filtrates were evaporated under reduced pressure to yield a dark oil, which after crystallisation from methanol gave 46.1 g of the title product (55% yield) as a yellow solid, m.p. 102°-104° C.

Workup

  1. temperatureat reflux for 3 hours
  2. customscreening, the filtrates were evaporated under reduced pressure
  3. customto yield a dark oil, which
  4. customafter crystallisation from methanol

Sources & evidence

ORD record
ord-37489464380644cc9a66aad3b4209dff
Source dataset
uspto-grants-1995_03
Patent number
US05395969

Reaction notes

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