Aniline → HCID 23175021, compound

HRID 1964758Notes

Reaction equation

HRID 1964758 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Br[C:9]1[CH:22]=[C:21]2[C:23]3=[C:24]4[C:14]([CH:15]=[CH:16][CH:17]=[C:18]4[CH:19]=[CH:20]2)=[CH:13][CH:12]=[C:11]3[CH:10]=1.C1C=CC(P(C2C(C3C(P(C4C=CC=CC=4)C4C=CC=CC=4)=CC=C4C=3C=CC=C4)=C3C(C=CC=C3)=CC=2)C2C=CC=CC=2)=CC=1.CC(C)([O-])C.[Na+]>C1(C)C=CC=CC=1>[C:2]1([NH:1][C:16]2[CH:15]=[C:14]3[C:24]4=[C:23]5[C:21]([CH:22]=[CH:9][CH:10]=[C:11]5[CH:12]=[CH:13]3)=[CH:20][CH:19]=[C:18]4[CH:17]=2)[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 6115AnilineHCID 634876Binap, (A+-)-HCID 3014034Pyrene, 2-bromo-HCID 23676156Sodium t-butoxide

Product 1

HCID 23175021HCID 23175021, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

In a three-neck-round floor flask of 250 ml, after 127.5 m mole of aniline, 102 m mole of 2-bromopyrene, 1.53 m mole of tris(dibenzyllidene acetone)dipalladium, 3.06 m mol of BINAP (2,2′-bis(disphenylphosphino)-1,1′-binaphthyl, and 132.6 m mole of sodium-tert-butoxide were melted in 100 mL of toluene and they were mixed for 24 hours in a bath of 1000, when a reaction was terminated, toluene was removed from a reaction mixture and then the reaction mixture was extracted using dichloromethane and water and distilled under a reduced pressure, a solvent of a solution passing through a silica gel column was distilled under a reduced pressure, and thus 5.5 g of an N-phenylpyrene-2-amine liquid was obtained.

Workup

  1. additionthey were mixed for 24 hours in a bath of 1000, when a reaction
  2. customwas terminated
  3. customtoluene was removed from a reaction mixture
  4. extractionthe reaction mixture was extracted
  5. distillationdistilled under a reduced pressure
  6. distillationwas distilled under a reduced pressure

Sources & evidence

ORD record
ord-63f6099d34e946238f523f05add33508
Source dataset
uspto-grants-2013_04
Patent number
US08415499B2

Reaction notes

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