Germane, chlorotris(1-methylethyl)- → 2-(3,5-Dimethylphenyl)-6-(triisopropylgermyl)quinoline

HRID 452354Notes

Reaction equation

Br[C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[N:8]=[C:7]([C:12]1[CH:17]=[C:16]([CH3:18])[CH:15]=[C:14]([CH3:19])[CH:13]=1)[CH:6]=[CH:5]2.[Li]CCCC.Cl[Ge:26]([CH:33]([CH3:35])[CH3:34])([CH:30]([CH3:32])[CH3:31])[CH:27]([CH3:29])[CH3:28]>C1COCC1>[CH3:19][C:14]1[CH:13]=[C:12]([C:7]2[CH:6]=[CH:5][C:4]3[C:9](=[CH:10][CH:11]=[C:2]([Ge:26]([CH:33]([CH3:35])[CH3:34])([CH:30]([CH3:32])[CH3:31])[CH:27]([CH3:29])[CH3:28])[CH:3]=3)[N:8]=2)[CH:17]=[C:16]([CH3:18])[CH:15]=1

Participants

Conditions

Temperature: -78 °C

Procedure

6-Bromo-2-(3,5-dimethylphenyl)quinoline (5.3 g, 16.98 mmol) and 150 mL anhydrous THF were added in a dry two-necked round bottom flask and cooled down to −78° C. 7.2 mL BuLi (2.5 M) was added dropwise. The solution was stirred for 45 minutes and 4.4 mL (20.37 mmol) of chlorotriisopropylgermane was slowly added with a syringe. The solution was stirred for 4 h and monitored by GC until the reaction was finished. The reaction mixture was purified by column and distillation. ˜6.1 g colorless liquid was obtained after distillation. GC-MS confirmed the desired product.

Workup

stirringThe solution was stirred for 4 h
distillationThe reaction mixture was purified by column and distillation

Sources & evidence

ORD record: ord-b48769045e0440e1bb5d5aaa82ab2620
Source dataset: uspto-grants-2013_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08492006B2

Reaction notes

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