Fluorene → HCID 15296112, compound

HRID 1463676Notes

Reaction equation

HRID 1463676 reaction equation
[CH:1]1[C:13]2[CH2:12][C:11]3[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=3)[C:5]=2[CH:4]=[CH:3][CH:2]=1.Cl.[N:15]1[CH:20]=[CH:19][CH:18]=[C:17]([CH2:21]Cl)[CH:16]=1.[OH-].[Na+]>[Br-].C([P+](CCCC)(CCCC)CCCC)CCCCCCCCCCCCCCC.C1(C)C=CC=CC=1>[N:15]1[CH:20]=[CH:19][CH:18]=[C:17]([CH2:21][C:12]2([CH2:21][C:17]3[CH:16]=[N:15][CH:20]=[CH:19][CH:18]=3)[C:11]3[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=3[C:5]3[C:13]2=[CH:1][CH:2]=[CH:3][CH:4]=3)[CH:16]=1

Participants

6

Reactant 3

HCID 6853FluoreneHCID 14798Sodium HydroxideHCID 233943-(Chloromethyl)pyridine hydrochloride

Product 1

HCID 15296112HCID 15296112, compound

Reagents, catalysts & solvents 2

HCID 84716Hexadecyltributylphosphonium bromideCatalystHCID 1140TolueneSolvent

Procedure

The title compound was prepared following the procedure described in Example 5 from 10.0 mmole of fluorene, 22.0 mmole of 3-picolylchloride hydrochloride, 2.0 mmole of cetyl tri-n-butyl phosphonium bromide, 20 ml of 50% sodium hydroxide and 40 ml of toluene by reaction at 50° for 6 hrs. The material was chromatographed (silica, CH2Cl2 /MeOH,95:5) to yield 2.6 g (70%), m.p. 137°-138°. δ: 3.41(s,4H), 6.71-6.97(m,4H), 7.17-7.35(tt,6H), 7.50-7.54(d,J=6.9 Hz, 2H), 7.91(s,2H), 8.12-8.15(d,J=5.4 Hz,2H). HRMS calculated for C25H20N2 : 348.1632 Found: 348.1626

Workup

  1. customThe material was chromatographed (silica, CH2Cl2 /MeOH,95:5)
  2. customto yield 2.6 g (70%), m.p. 137°-138°

Sources & evidence

ORD record
ord-5fe7ad77d5ab43ccb69dca89480851be
Source dataset
uspto-grants-1994_04
Patent number
US05300642

Reaction notes

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