Aniline → HCID 57816297, compound

HRID 2275920Notes

Reaction equation

HRID 2275920 reaction equation
Br[C:2]1[C:14]2[C:13]([C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=3)([C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=3)[C:12]3[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=3)[C:6]=2[CH:5]=[CH:4][CH:3]=1.[NH2:27][C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=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:21]1([C:13]2([C:15]3[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=3)[C:14]3[CH:2]=[C:3]([NH:27][C:28]4[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=4)[CH:4]=[CH:5][C:6]=3[C:7]3[C:12]2=[CH:11][CH:10]=[CH:9][CH:8]=3)[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1

Participants

7

Reactant 3

HCID 6115AnilineHCID 23676156Sodium t-butoxideHCID 667978339H-Fluorene, 1-bromo-9,9-diphenyl-

Product 1

HCID 57816297HCID 57816297, compound

Reagents, catalysts & solvents 3

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

Procedure

40 g of bromo-9,9-diphenyl-9H-fluorene (100.7 mmol), 12 ml of aniline (121 mmol), 0.85 g of DPPF (1.5 mmol), 0.3 g of palladium(II)acetate and 25 g of sodium tert-butoxide (262 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 26.8 g (65 mmol, 65%).

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-01eab0d60e804bd7b57d67260567a2a6
Source dataset
uspto-grants-2015_09
Patent number
US09126970B2

Reaction notes

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