Dichlorodiphenylsilane → HCID 90386979, compound

HRID 1424764Notes

Reaction equation

HRID 1424764 reaction equation
[CH:1]1[C:13]2[N:12]([C:14]3[CH:15]=[C:16]([N:20]([C:28]4[CH:33]=[CH:32][CH:31]=[CH:30][C:29]=4Br)[C:21]4[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=4Br)[CH:17]=[CH:18][CH:19]=3)[C:11]3[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=3)[C:5]=2[CH:4]=[CH:3][CH:2]=1.C([Li])CCC.Cl[Si:41](Cl)([C:48]1[CH:53]=[CH:52][CH:51]=[CH:50][CH:49]=1)[C:42]1[CH:47]=[CH:46][CH:45]=[CH:44][CH:43]=1>C1COCC1>[CH:1]1[C:13]2[N:12]([C:14]3[CH:15]=[C:16]([N:20]4[C:28]5[CH:33]=[CH:32][CH:31]=[CH:30][C:29]=5[Si:41]([C:48]5[CH:49]=[CH:50][CH:51]=[CH:52][CH:53]=5)([C:42]5[CH:47]=[CH:46][CH:45]=[CH:44][CH:43]=5)[C:22]5[CH:23]=[CH:24][CH:25]=[CH:26][C:21]4=5)[CH:17]=[CH:18][CH:19]=3)[C:11]3[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=3)[C:5]=2[CH:4]=[CH:3][CH:2]=1

Participants

5

Reactant 3

HCID 6627DichlorodiphenylsilaneHCID 90387545HCID 90387545, compoundHCID 178418339Butyllithium

Product 1

HCID 90386979HCID 90386979, compoundYield 33%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-78 °C

Procedure

N-(3-(9H-carbazol-9-yl)phenyl)-2-bromo-N-(2-bromophenyl)aniline (4.05 g, 7.13 mmol) was added into a 250-mL round bottom flask and solubilized in dry THF (100 ml). The mixture was cooled down to −78° C. Butyllithium (5.70 ml, 14.25 mmol) was added dropwise. The mixture was stirred at −78° C. for 2 hours. Dichlorodiphenylsilane (1.467 ml, 7.13 mmol) was then added dropwise. The mixture was warmed to room temperature and stirred overnight. The reaction mixture was quenched with water, extracted three times with diethyl ether and washed three times with water. The crude material was purified by column chromatography using hexane and dichloromethane (85/15) as the eluent. After most of the impurities came out, the eluent was gradually changed to 25% dichloromethane in hexane. The white powder was then triturated in acetone and then recrystallized three times from dichloromethane and hexane. 1.5 g of 5-(3-(9H-carbazol-9-yl)phenyl)-10,10-diphenyl-5,10-dihydrodibenzo[b,e][1,4]azasiline was sublimed to afford 1.4 g yield of 33%.

Workup

  1. temperatureThe mixture was warmed to room temperature
  2. stirringstirred overnight
  3. customThe reaction mixture was quenched with water
  4. extractionextracted three times with diethyl ether
  5. washwashed three times with water
  6. customThe crude material was purified by column chromatography
  7. customThe white powder was then triturated in acetone
  8. customrecrystallized three times from dichloromethane and hexane
  9. customto afford 1.4 g yield of 33%

Sources & evidence

ORD record
ord-1c60893bb1f74b70955a9892566cff16
Source dataset
uspto-grants-2015_01
Patent number
US08927749B2

Reaction notes

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