Chlorotrimethylgermane → HCID 86669968, compound

HRID 452352

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]([CH3:29])([CH3:28])[CH3:27]>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]([CH3:29])([CH3:28])[CH3:27])[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 (6.0 g, 19.2 mmol) and 150 mL anhydrous THF were added in a dry 2-necked round bottom flask and cooled down to −78° C. 8.46 mL BuLi (2.5 M in hexane) was added dropwise. The solution was stirred for 45 minutes at −78° C. and 2.83 mL (23.06 mmol) of chlorotrimethylgermane was slowly added with a syringe. The solution was stirred for overnight. The reaction mixture was purified by column 5% ethyl acetate in hexane and distillation. ˜4.1 g white slide was obtained after recrystallization from hexane. GC-MS confirmed the desired product.

Workup

stirringThe solution was stirred for overnight
distillationThe reaction mixture was purified by column 5% ethyl acetate in hexane and distillation
custom˜4.1 g white slide was obtained
customafter recrystallization from hexane

Sources & evidence

ORD record: ord-d8535ac3f80b4ef29b8ad6cf130827e7
Source dataset: uspto-grants-2013_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08492006B2

Linked notes

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