Magnesium → HCID 178447756, compound

HRID 1080590Notes

Reaction equation

HRID 1080590 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].[CH3:17][CH:18]([CH3:36])[CH2:19][CH2:20][Si@H:21]1[CH2:26][CH2:25][C@H:24]([CH2:27][CH2:28][CH:29]2[CH2:34][CH2:33][CH:32](Br)[CH2:31][CH2:30]2)[CH2:23][CH2:22]1>[Cu]Cl.C1COCC1>[CH3:17][CH:18]([CH3:36])[CH2:19][CH2:20][Si@H:21]1[CH2:22][CH2:23][C@H:24]([CH2:27][CH2:28][C@H:29]2[CH2:30][CH2:31][C@H:32]([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)[CH2:33][CH2:34]2)[CH2:25][CH2:26]1

Participants

6

Reactant 3

HCID 5462224MagnesiumHCID 23364718HCID 23364718, compoundHCID 178447743HCID 178447743, compound

Product 1

HCID 178447756HCID 178447756, compoundYield 73%

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 85.9 g (0.1 mol) of 4-(2-(trans-4-(3-methylbutyl)-4-silacyclohexyl)ethyl)cyclohexyl bromide. After a conventional after treatment, 4-(trans-4-(2-(trans-4-(3-methylbutyl)-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 34.2 g (yield 73.0%) of the trans isomer.

Workup

  1. customto obtain a Grignard's reagent

Sources & evidence

ORD record
ord-ac2bb938f187463c8ea280dc6060e5ec
Source dataset
uspto-grants-1996_12
Patent number
US05582764

Reaction notes

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