2-Chloroaniline → HCID 118292559, compound

HRID 1483885Notes

Reaction equation

HRID 1483885 reaction equation
Br[C:2]1[CH:3]=[CH:4][C:5]2[C:6]3[C:11]([C:12]4[C:17]=2[C:16]=1[CH:15]=[CH:14][CH:13]=4)=[CH:10][CH:9]=[CH:8][CH:7]=3.[Cl:18][C:19]1[CH:25]=[CH:24][CH:23]=[CH:22][C:20]=1[NH2:21].C(P(C(C)(C)C)C(C)(C)C)(C)(C)C.CC(C)([O-])C.[Na+]>[Pd].[Pd].C(=CC(C=CC1C=CC=CC=1)=O)C1C=CC=CC=1.C(=CC(C=CC1C=CC=CC=1)=O)C1C=CC=CC=1.C(=CC(C=CC1C=CC=CC=1)=O)C1C=CC=CC=1.C1(C)C=CC=CC=1>[Cl:18][C:19]1[CH:25]=[CH:24][CH:23]=[CH:22][C:20]=1[NH:21][C:2]1[CH:3]=[CH:4][C:5]2[C:6]3[C:11]([C:12]4[C:17]=2[C:16]=1[CH:15]=[CH:14][CH:13]=4)=[CH:10][CH:9]=[CH:8][CH:7]=3

Participants

7

Reactant 4

HCID 72402-ChloroanilineHCID 83681Tris(1,1-dimethylethyl)phosphineHCID 132218003-BromofluorantheneHCID 23676156Sodium t-butoxide

Product 1

HCID 118292559HCID 118292559, compoundYield 75.2%

Reagents, catalysts & solvents 2

HCID 9832798Tris(dibenzylideneacetone) dipalladiumCatalystHCID 1140TolueneSolvent

Conditions

Temperature
80 °C

Procedure

Under an argon atmosphere, 7.0 g of 3-bromofluoranthene, 4.76 g of 2-chloroaniline, 0.46 g of tris(dibenzylideneacetone) dipalladium(0), 0.58 g of tri-t-butylphosphine tetrafluorohydroborate, 3.4 g of sodium t-butoxide, and 200 mL of dry toluene were charged in a flask, and the resultant mixture was stirred under heating at 80° C. for 8 h. After cooling to room temperature, the reaction solution was extracted with toluene and the extract was filtered through celite. The filtrate was concentrated and the residue was purified by silica gel column chromatography to obtain 6.14 g of 3-(2-chloroanilino)fluoranthene (yield: 75%).

Workup

  1. temperatureAfter cooling to room temperature
  2. extractionthe reaction solution was extracted with toluene
  3. filtrationthe extract was filtered through celite
  4. concentrationThe filtrate was concentrated
  5. customthe residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-b22878628d1b4d45b2e2def543d69a26
Source dataset
uspto-grants-2016_08
Patent number
US09419226B2

Reaction notes

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