Magnesium → HCID 178444579, compound

HRID 2258169Notes

Reaction equation

HRID 2258169 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:13]=[CH:12][C:11]([CH2:14][CH2:15][CH3:16])=[CH:10][C:9]=2[F:17])=[C:4]([F:18])[CH:3]=1.[Mg].[CH2:20]([CH:25]1[CH2:30][CH2:29][SiH:28](OC)[CH2:27][CH2:26]1)[CH2:21][CH2:22][CH2:23][CH3:24]>C1COCC1>[CH2:20]([C@H:25]1[CH2:26][CH2:27][Si@H:28]([C:2]2[CH:7]=[CH:6][C:5]([C:8]3[CH:13]=[CH:12][C:11]([CH2:14][CH2:15][CH3:16])=[CH:10][C:9]=3[F:17])=[C:4]([F:18])[CH:3]=2)[CH2:29][CH2:30]1)[CH2:21][CH2:22][CH2:23][CH3:24]

Participants

5

Reactant 3

HCID 5462224MagnesiumHCID 22924589HCID 22924589, compoundHCID 123842306HCID 123842306, compound

Product 1

HCID 178444579HCID 178444579, compoundYield 80%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

6.2 g (20 mmol) of 4-bromo-2,2'-difluoro-4'-propylbiphenyl was dripped into a mixture of 0.5 g of magnesium (21 mmol) and 50 ml of THF to obtain a Grignard's reagent. This solution was then dripped into a 50 ml THF solution of 4.0 g (20 mmol) of 4-n-pentyl-1-methoxy-1-silacyclohexane to obtain 4'-(trans-4-n-pentyl-1-silacyclohexyl)-2,2'-difluoro-4-propylbiphenyl. The silacyclohexane rings of this product were a mixture of trans isomers and cis isomers. They were separated by means of chromatography to obtain 6.4 g of the trans isomers (yield 80%).

Workup

  1. customto obtain a Grignard's reagent

Sources & evidence

ORD record
ord-8266e0b158d54fa9a5c20b51726d26a1
Source dataset
uspto-grants-1997_08
Patent number
US05659059

Reaction notes

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