2-Bromo-9H-fluorene → HCID 19922464, compound

HRID 1463669Notes

Reaction equation

HRID 1463669 reaction equation
[Br:1][C:2]1[CH:14]=[CH:13][C:12]2[C:11]3[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=3)[CH2:5][C:4]=2[CH:3]=1.[ClH:15].[N:16]1[CH:21]=[CH:20][C:19]([CH2:22][Cl:23])=[CH:18][CH:17]=1.[OH-].[Na+]>[Br-].C([P+](CCCC)(CCCC)CCCC)CCCCCCCCCCCCCCC.C1(C)C=CC=CC=1>[ClH:23].[ClH:15].[N:16]1[CH:21]=[CH:20][C:19]([CH2:22][C:5]2([CH2:22][C:19]3[CH:20]=[CH:21][N:16]=[CH:17][CH:18]=3)[C:4]3[CH:3]=[C:2]([Br:1])[CH:14]=[CH:13][C:12]=3[C:11]3[C:6]2=[CH:7][CH:8]=[CH:9][CH:10]=3)=[CH:18][CH:17]=1

Participants

6

Reactant 3

HCID 143362-Bromo-9H-fluoreneHCID 14798Sodium HydroxideHCID 745704-(Chloromethyl)pyridinium chloride

Product 1

HCID 19922464HCID 19922464, compound

Reagents, catalysts & solvents 2

HCID 84716Hexadecyltributylphosphonium bromideCatalystHCID 1140TolueneSolvent

Procedure

The title compound was prepared following the procedure of Example 5 from 1.0 g (4.08 mmole) of 2-bromofluorene, 1.5 g of 4-picolylchloride hydrochloride, 100 mg of cetyl tri-n-butyl phosphonium bromide, 20 ml of 50% sodium hydroxide solution, and 20 ml toluene by reaction at 50° for 1 hr. The product was chromatographed (silica, CH2Cl2 /CH3OH, 100:1), m.p. (dihydrochloride) >300° NMR (200 MHz,CDCL3) δ: 3.39(dd,4H), 6.48(d,4H), 7.10-7.67 (m,7H-arom.), 8.12(d,J=5.7 Hz,4H). HRMS calculated for C25H19BrN2 : 426.0758 Found: 426.0758

Workup

  1. customby reaction at 50° for 1 hr
  2. customThe product was chromatographed (silica, CH2Cl2 /CH3OH, 100:1), m.p. (dihydrochloride) >300° NMR (200 MHz,CDCL3) δ: 3.39(dd,4H), 6.48(d,4H), 7.10-7.67 (m,7H-arom.), 8.12(d,J=5.7 Hz,4H)

Sources & evidence

ORD record
ord-2859b61345524bccae8b0f1802bd7f0e
Source dataset
uspto-grants-1994_04
Patent number
US05300642

Reaction notes

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