4-Aminobiphenyl → N-(biphenyl-4-yl)-9,9-dimethyl-9H-fluoren-2-amine

HRID 2275917Notes

Reaction equation

HRID 2275917 reaction equation
Br[C:2]1[C:14]2[C:13]([CH3:16])([CH3:15])[C:12]3[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=3)[C:6]=2[CH:5]=[CH:4][CH:3]=1.[C:17]1([C:23]2[CH:29]=[CH:28][C:26]([NH2:27])=[CH:25][CH:24]=2)[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=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>[C:23]1([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[CH:24]=[CH:25][C:26]([NH:27][C:3]2[CH:4]=[CH:5][C:6]3[C:7]4[C:12](=[CH:11][CH:10]=[CH:9][CH:8]=4)[C:13]([CH3:16])([CH3:15])[C:14]=3[CH:2]=2)=[CH:28][CH:29]=1

Participants

7

Reactant 3

HCID 71024-AminobiphenylHCID 23676156Sodium t-butoxideHCID 667979641-bromo-9,9-dimethyl-9H-fluorene

Product 1

HCID 20730584N-(biphenyl-4-yl)-9,9-dimethyl-9H-fluoren-2-amine

Reagents, catalysts & solvents 3

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

Procedure

50 g of bromo-9,9-dimethyl-9H-fluorene (183 mmol), 38 g of p-phenylaniline (220 mmol), 1.5 g of DPPF (2.7 mmol), 0.5 g of palladium(II)acetate and 45 g of sodium tert-butoxide (486 mmol) are heated at the boil in 1.5 l of toluene under a protective-gas atmosphere for 18 h. The mixture is subsequently partitioned between toluene and water, and 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 33 g (91.5 mmol, 50%).

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-1dc11bb1ee244a75885ea59be3b15e5f
Source dataset
uspto-grants-2015_09
Patent number
US09126970B2

Reaction notes

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