2-Bromo-9,9-dimethylfluorene → N-(9,9-Dimethyl-9H-fluoren-2-yl)-9,9-dimethyl-9H-fluoren-2-amine

HRID 2275954Notes

Reaction equation

HRID 2275954 reaction equation
Br[C:2]1[CH:14]=[CH:13][C:12]2[C:11]3[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=3)[C:5]([CH3:16])([CH3:15])[C:4]=2[CH:3]=1.[NH2:17][C:18]1[CH:30]=[CH:29][C:28]2[C:27]3[C:22](=[CH:23][CH:24]=[CH:25][CH:26]=3)[C:21]([CH3:32])([CH3:31])[C:20]=2[CH:19]=1.CC(C)([O-])C.[Na+]>C1(C)C=CC=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.[Fe+2].C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[CH3:15][C:5]1([CH3:16])[C:4]2[CH:3]=[C:2]([NH:17][C:18]3[CH:30]=[CH:29][C:28]4[C:27]5[C:22](=[CH:23][CH:24]=[CH:25][CH:26]=5)[C:21]([CH3:32])([CH3:31])[C:20]=4[CH:19]=3)[CH:14]=[CH:13][C:12]=2[C:11]2[C:6]1=[CH:7][CH:8]=[CH:9][CH:10]=2

Participants

7

Reactant 3

HCID 109456062-Bromo-9,9-dimethylfluoreneHCID 226170939,9-Dimethyl-9H-fluoren-2-amineHCID 23676156Sodium t-butoxide

Product 1

HCID 59254080N-(9,9-Dimethyl-9H-fluoren-2-yl)-9,9-dimethyl-9H-fluoren-2-amine

Reagents, catalysts & solvents 3

HCID 167845palladium(II) acetateCatalystHCID 635956Ferrocene-1,1'-bis-(diphenylphosphine)CatalystHCID 1140TolueneSolvent

Procedure

81 g of 2-bromo-9,9-dimethyl-9H-fluorene (300 mmol), 93 g of 2-amino-9,9-dimethyl-9H-fluorene (444 mmol), 5 g of DPPF (9 mmol), 2 g of palladium(II) acetate and 86 g of sodium tert-butoxide (486 mmol) are heated at the boil for 18 h in 1.5 l of toluene under a protective-gas atmosphere. The mixture is subsequently partitioned between toluene and water, the organic phase is washed three times with water, dried over Na2SO4 and evaporated in a rotary evaporator. The residue which remains is recrystallised from heptane/ethyl acetate. The yield is 93 g (231 mmol, 77%).

Workup

  1. customThe mixture is subsequently partitioned between toluene and water
  2. washthe organic phase is washed three times with water
  3. dry with materialdried over Na2SO4
  4. customevaporated in a rotary evaporator
  5. customThe residue which remains is recrystallised from heptane/ethyl acetate

Sources & evidence

ORD record
ord-69305166c08b428fb13362d96d027658
Source dataset
uspto-grants-2015_09
Patent number
US09126970B2

Reaction notes

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