Allyl bromide → HCID 18759629, compound

HRID 432550Notes

Reaction equation

HRID 432550 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:21]3[C:12](=[C:13]4[C:18](=[CH:19][CH:20]=3)[C:17]([C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=3)=[CH:16][CH:15]=[N:14]4)[N:11]=[CH:10][CH:9]=2)=[CH:4][CH:3]=1.[CH2:28](Br)[CH:29]=[CH2:30]>COCCOC.C1(C)C=CC=CC=1>[CH2:30]([O:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[C:21]3[C:12](=[C:13]4[C:18](=[CH:19][CH:20]=3)[C:17]([C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=3)=[CH:16][CH:15]=[N:14]4)[N:11]=[CH:10][CH:9]=2)=[CH:6][CH:7]=1)[CH:29]=[CH2:28]

Participants

5

Reactant 2

HCID 7841Allyl bromideHCID 136330640HCID 136330640, compound

Product 1

HCID 18759629HCID 18759629, compound

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 80711,2-DimethoxyethaneSolvent2×

Conditions

Temperature
35 °C

Procedure

4-p-hydroxyphenyl-7-phenyl-1,10-phenanthroline (0. 348 g) is reacted with Na metal (0.023 g) in ethylene glycol dimethyl ether (100 mL). To this mixture is added a solution of allylbromide (0.125 g) in ethylene glycol dimethyl ether (10 mL). The resulting mixture is stirred at 35° C. for 24 hours, or until the reaction is judged complete by TLC. The reaction mixture is diluted with toluene, washed with 10% NaOH, washed with water and dried over MgSO4. Roto-evaporation of the solvent gives a residue that is purified by column chromatography on silica gel.

Workup

  1. washwashed with 10% NaOH
  2. washwashed with water
  3. dry with materialdried over MgSO4
  4. customRoto-evaporation of the solvent
  5. customgives a residue that
  6. customis purified by column chromatography on silica gel

Sources & evidence

ORD record
ord-3d34a1e90d57413998246eb53fd85a10
Source dataset
uspto-grants-2003_12
Patent number
US06664111B2

Reaction notes

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