Water → HCID 86632978, compound

HRID 549486Notes

Reaction equation

HRID 549486 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][C:5]2[C:18]3[N:17]=[C:16]([C:19]4[C:24]([Br:25])=[CH:23][CH:22]=[CH:21][C:20]=4[Br:26])[NH:15][C:14]=3[C:13]3[C:8](=[CH:9][C:10]([Br:27])=[CH:11][CH:12]=3)[C:6]=2[CH:7]=1.[H-].[Na+].[CH3:30][Si:31]([CH2:34][CH2:35][O:36][CH2:37]Cl)([CH3:33])[CH3:32].O>C1COCC1>[Br:27][C:10]1[CH:11]=[CH:12][C:13]2[C:14]3[N:15]=[C:16]([C:19]4[C:24]([Br:25])=[CH:23][CH:22]=[CH:21][C:20]=4[Br:26])[N:17]([CH2:37][O:36][CH2:35][CH2:34][Si:31]([CH3:33])([CH3:32])[CH3:30])[C:18]=3[C:5]3[C:6](=[CH:7][C:2]([Br:1])=[CH:3][CH:4]=3)[C:8]=2[CH:9]=1

Participants

6

Reactant 4

HCID 962WaterHCID 24758Sodium hydrideHCID 27242712-Chloromethyl 2-(trimethylsilyl)ethyl etherHCID 86632979HCID 86632979, compound

Product 1

HCID 86632978HCID 86632978, compoundYield 96.6%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

To a suspension of 6,9-dibromo-2-(2,6-dibromophenyl)-1H-phenanthro[9,10-d]imidazole from Step 1 (61.8 g, 0.1 mol) in THF (980 mL) at 0° C., was added sodium hydride (60% dispersion in mineral oil, 10 g, 0.25 mol). The suspension was stirred at 0° C. for 15 minutes, followed by addition of SEMCl (45 mL, 0.25 mol). The mixture was warmed to room temperature and stirred for 3 h, after which it was poured into water. The aqueous phase was extracted with ethyl acetate, the organic layer washed once with brine, dried over Na2SO4, filtered and concentrated. The crude material was swished in hexanes/diethyl ether for 4 h, then filtered to obtain 6,9-dibromo-2-(2,6-dibromophenyl)-1-{[2-(trimethylsilyl)ethoxy]methyl}-1H-phenanthro[9,10-d]imidazole as a beige powder (71.5 g, 95%).

Workup

  1. temperatureThe mixture was warmed to room temperature
  2. stirringstirred for 3 h
  3. extractionThe aqueous phase was extracted with ethyl acetate
  4. washthe organic layer washed once with brine
  5. dry with materialdried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated
  8. waitThe crude material was swished in hexanes/diethyl ether for 4 h
  9. filtrationfiltered

Sources & evidence

ORD record
ord-11362ad7a9804e0b9ea7f477f4dda548
Source dataset
uspto-grants-2011_05
Patent number
US07943649B2

Reaction notes

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