Sodium Hydroxide → HCID 15296111, compound

HRID 1648144Notes

Reaction equation

HRID 1648144 reaction equation
[F:1][CH:2]([F:16])[C:3]1[CH:15]=[CH:14][C:13]2[C:12]3[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=3)[CH2:6][C:5]=2[CH:4]=1.Cl.[N:18]1[CH:23]=[CH:22][C:21]([CH2:24]Cl)=[CH:20][CH:19]=1.[OH-].[Na+]>[Cl-].C([N+](CC)(CC)CC)C1C=CC=CC=1.C1(C)C=CC=CC=1>[N:18]1[CH:23]=[CH:22][C:21]([CH2:24][C:6]2([CH2:24][C:21]3[CH:22]=[CH:23][N:18]=[CH:19][CH:20]=3)[C:5]3[CH:4]=[C:3]([CH:2]([F:16])[F:1])[CH:15]=[CH:14][C:13]=3[C:12]3[C:7]2=[CH:8][CH:9]=[CH:10][CH:11]=3)=[CH:20][CH:19]=1

Participants

6

Reactant 3

HCID 14798Sodium HydroxideHCID 745704-(Chloromethyl)pyridinium chlorideHCID 19922436HCID 19922436, compound

Product 1

HCID 15296111HCID 15296111, compound

Reagents, catalysts & solvents 2

HCID 66133Benzyl triethylammonium chlorideCatalystHCID 1140TolueneSolvent

Procedure

The title compound was prepared following the method of Example 1 from 0.6 g (2.78 mole) of 2-difluoromethylfluorene, 1.14 g of 4-picolylchloride hydrochloride, 32 mg benzyltriethylammonium chloride, 4 ml of 50% sodium hydroxide solution, and 25 ml of toluene by reaction at 50° for 6 hrs. The product was chromatographed (silica, CH2Cl2 /MeOH, 10:1) to yield 0.5 g, m.p. >300°; NMR (CDCl3, 200 MHz) δ: 3.43(S,4H), 6.45(d,J=5.7 Hz,4H), 6.74(t,J=56.6 Hz,1H), 7.26-7.70(m.arom.), 8.1(d,J=5.7 Hz,4H). HRMS calculated for C26H20N2F2 : 398.1595 Found: 398.1583.

Workup

  1. customby reaction at 50° for 6 hrs
  2. customThe product was chromatographed (silica, CH2Cl2 /MeOH, 10:1)
  3. customto yield 0.5 g, m.p. >300°

Sources & evidence

ORD record
ord-65da1cece7364d2ea209aa5c32715d48
Source dataset
uspto-grants-1995_07
Patent number
US05434264

Reaction notes

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