N-bromobutanimide → 10-Biphenyl-4-yl-7-bromo-12,12-dimethyl-10,12-dihydro-10-azaindeno[2,1-b]fluorene

HRID 2275937Notes

Reaction equation

HRID 2275937 reaction equation
[C:1]1([C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=2)[CH:6]=[CH:5][C:4]([N:7]2[C:19]3[CH:18]=[C:17]4[C:20]([CH3:28])([CH3:27])[C:21]5[C:26]([C:16]4=[CH:15][C:14]=3[C:13]3[C:8]2=[CH:9][CH:10]=[CH:11][CH:12]=3)=[CH:25][CH:24]=[CH:23][CH:22]=5)=[CH:3][CH:2]=1.[Br:35]N1C(=O)CCC1=O>C(#N)C>[C:1]1([C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=2)[CH:2]=[CH:3][C:4]([N:7]2[C:19]3[CH:18]=[C:17]4[C:20]([CH3:27])([CH3:28])[C:21]5[C:26]([C:16]4=[CH:15][C:14]=3[C:13]3[C:8]2=[CH:9][CH:10]=[C:11]([Br:35])[CH:12]=3)=[CH:25][CH:24]=[CH:23][CH:22]=5)=[CH:5][CH:6]=1

Participants

4

Reactant 2

HCID 67184N-bromobutanimideHCID 6679777010-Biphenyl-4-yl-12,12-dimethyl-10,12-dihydro-10-azaindeno[2,1-b]fluorene

Product 1

HCID 6679773810-Biphenyl-4-yl-7-bromo-12,12-dimethyl-10,12-dihydro-10-azaindeno[2,1-b]fluoreneYield 53%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

17.5 g (40.18 mmol) of 10-biphenyl-4-yl-12,12-dimethyl-10,12-dihydro-10-azaindeno[2,1-b]fluorene are suspended in 450 ml of acetonitrile, and 7.15 g (40.18 mmol) of N-bromosuccinimide are added in portions at −20° C. at such a rate that the reaction temperature does not rise above −20° C. The mixture is stirred for a further 18 h, during which the temperature is allowed to come to RT. The reaction mixture is subsequently evaporated in a rotary evaporator, dissolved in dichloromethane and washed with water. The residue is dried, evaporated and subsequently recrystallised from toluene to a purity of 99.3%, giving 10.9 g (53%) of the product as a white solid.

Workup

  1. customdoes not rise above −20° C
  2. customto come to RT
  3. customThe reaction mixture is subsequently evaporated in a rotary evaporator
  4. dissolutiondissolved in dichloromethane
  5. washwashed with water
  6. customThe residue is dried
  7. customevaporated
  8. customsubsequently recrystallised from toluene to a purity of 99.3%

Sources & evidence

ORD record
ord-bbf0870b4dc54aa5893df49474721fb9
Source dataset
uspto-grants-2015_09
Patent number
US09126970B2

Reaction notes

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