Magnesium → HCID 178447757, compound

HRID 1080589Notes

Reaction equation

HRID 1080589 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:13]=[CH:12][C:11]([F:14])=[C:10]([F:15])[CH:9]=2)=[CH:4][CH:3]=1.[Mg].[CH2:17]([Si@H:22]1[CH2:27][CH2:26][C@H:25]([CH2:28][CH2:29][CH:30]2[CH2:35][CH2:34][CH:33](Br)[CH2:32][CH2:31]2)[CH2:24][CH2:23]1)[CH2:18][CH2:19][CH2:20][CH3:21]>[Cu]Cl.C1COCC1>[CH2:17]([Si@H:22]1[CH2:23][CH2:24][C@H:25]([CH2:28][CH2:29][C@H:30]2[CH2:35][CH2:34][C@H:33]([C:2]3[CH:7]=[CH:6][C:5]([C:8]4[CH:13]=[CH:12][C:11]([F:14])=[C:10]([F:15])[CH:9]=4)=[CH:4][CH:3]=3)[CH2:32][CH2:31]2)[CH2:26][CH2:27]1)[CH2:18][CH2:19][CH2:20][CH3:21]

Participants

6

Reactant 3

HCID 5462224MagnesiumHCID 23364718HCID 23364718, compoundHCID 178447744HCID 178447744, compound

Product 1

HCID 178447757HCID 178447757, compoundYield 76.9%

Reagents, catalysts & solvents 2

HCID 62652Cuprous chlorideCatalystHCID 8028TetrahydrofuranSolvent2×

Procedure

26.9 g (0.1 mol) of 4-bromo-3',4'-difluorobiphenyl was dripped into a mixture of 2.5 g (0.11 mol) of magnesium and 300 ml of THF to obtain a Grignard's reagent. This solution was then dripped into a 500 ml THF solution of 0.5 g of copper (I) chloride and 35.9 g (0.1 mol) of 4-(2-(trans-4-n-pentyl-4-silacyclohexyl)ethyl)cyclohexyl bromide. After a conventional after treatment, 4-(trans-4-(2-(trans-4-n-pentyl-4-silacyclohexyl)ethyl)cyclohexyl)-3',4'-difluorobiphenyl was obtained. The silacyclohexane rings of the product were a mixture of trans isomers and cis isomers. They were separated by means of chromatography to obtain 36.0 g (yield 76.9%) of the trans isomer.

Workup

  1. customto obtain a Grignard's reagent

Sources & evidence

ORD record
ord-ed64cae0586a4a568d9d46427a52cfec
Source dataset
uspto-grants-1996_12
Patent number
US05582764

Reaction notes

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