Cyanuric fluoride → HCID 131723870, compound

HRID 1268494Notes

Reaction equation

HRID 1268494 reaction equation
Br[C:2]1[CH:14]=[CH:13][C:12]2[C:11]3[C:6](=[CH:7][C:8]([N:15]([C:22]4[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=4)[C:16]4[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=4)=[CH:9][CH:10]=3)[C:5]([CH2:31][CH:32]=[CH2:33])([CH2:28][CH:29]=[CH2:30])[C:4]=2[CH:3]=1.C([Li])CCC.[N:39]1[C:46](F)=[N:45][C:43](F)=[N:42][C:40]=1F>C1COCC1.C1(C)C=CC=CC=1.O>[C:22]1([N:15]([C:16]2[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=2)[C:8]2[CH:7]=[C:6]3[C:11]([C:12]4[CH:13]=[CH:14][C:2]([C:40]5[N:42]=[CH:43][N:45]=[CH:46][N:39]=5)=[CH:3][C:4]=4[C:5]3([CH2:31][CH:32]=[CH2:33])[CH2:28][CH:29]=[CH2:30])=[CH:10][CH:9]=2)[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=1

Participants

7

Reactant 3

HCID 12664Cyanuric fluorideHCID 18544379HCID 18544379, compoundHCID 178418339Butyllithium

Product 1

HCID 131723870HCID 131723870, compoundYield 60%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 1140TolueneSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of 2-bromo-7-(diphenylamino)-9,9-diprop-2 -enylfluorene (22.16 g, 0.045 mol), in THF (200 mL), cooled in a dry ice-acetone bath, a solution of n-butyl lithium in hexanes (1.6M, 30 mL, 0.048 mol), was added by syringe over 5 minutes. After 25 minutes, over a 30 minute period, a solution of cyanuric fluoride (2.025 g, 0.015 mol), in THF (100 mL) was added to result in a greenish fluorescent solution, which turned orange at the end of additon. The mixture was allowed to warm up slowly to room temperature, diluted with toluene and water, and the organic phase was dried and concentrated. The residue was chromatographed over alumina (eluted with 1:3 toluene-heptane), rechromatographed over silica gel (eluted with 1:3 toluene-heptane), and then crystallized from 1:3 toluene-heptane. The desired product was obtained as a bright yellow solids, 11.84 g, 60% yield, m.p. 235-237° C. Recrystallization from 2:1 heptane-toluene raised its m.p. to 236-238° C. Mass Spec: m/z 1314 (M+). Anal. Calcd. for C96H78N6: C, 87.64%; H, 5.90%: N, 6.3%. Found: C, 87.59%; H, 6.06%; N, 6.15%.

Workup

  1. waitover a 30 minute period
  2. customto result in a greenish fluorescent solution, which
  3. customthe organic phase was dried
  4. concentrationconcentrated
  5. customThe residue was chromatographed over alumina (eluted with 1:3 toluene-heptane)
  6. customrechromatographed over silica gel (eluted with 1:3 toluene-heptane)
  7. customcrystallized from 1:3 toluene-heptane

Sources & evidence

ORD record
ord-412219c5e44f497da56ccfc5ab19f835
Source dataset
uspto-grants-2003_04
Patent number
US06555682B1

Reaction notes

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