Magnesium → HCID 178447763, compound

HRID 1080588Notes

Reaction equation

HRID 1080588 reaction equation
[CH2:1]([Si@H:6]1[CH2:11][CH2:10][C@H:9]([CH2:12][CH2:13][CH:14]2[CH2:19][CH2:18][CH:17](Br)[CH2:16][CH2:15]2)[CH2:8][CH2:7]1)[CH2:2][CH2:3][CH2:4][CH3:5].[Mg].Br[C:23]1[CH:28]=[C:27]([F:29])[C:26]([C:30]2[CH:35]=[C:34]([F:36])[C:33]([O:37][CH:38]([F:40])[F:39])=[C:32]([F:41])[CH:31]=2)=[C:25]([F:42])[CH:24]=1>C1COCC1>[CH2:1]([Si@H:6]1[CH2:11][CH2:10][C@H:9]([CH2:12][CH2:13][C@H:14]2[CH2:19][CH2:18][C@H:17]([C:23]3[CH:24]=[C:25]([F:42])[C:26]([C:30]4[CH:31]=[C:32]([F:41])[C:33]([O:37][CH:38]([F:39])[F:40])=[C:34]([F:36])[CH:35]=4)=[C:27]([F:29])[CH:28]=3)[CH2:16][CH2:15]2)[CH2:8][CH2:7]1)[CH2:2][CH2:3][CH2:4][CH3:5]

Participants

5

Reactant 3

HCID 5462224MagnesiumHCID 23364821HCID 23364821, compoundHCID 178447744HCID 178447744, compound

Product 1

HCID 178447763HCID 178447763, compoundYield 70.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

36.0 g (0.1 mol) of 4-(2-(trans-4-n-pentyl-4-silacyclohexyl)ethyl)cyclohexyl bromide 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 tetrakis triphenylphosphine palladium and 87.1 g (0.1 mol) of 4-bromo-2,6,3',5'-tetrafluoro-4'-difluoromethoxybiphenyl. After a conventional after treatment, 4-(trans-4-(2-(trans-4-n-pentyl-4-silacyclohexyl)ethyl)cyclohexyl)-2,6,3',5'-tetrafluoro-4'-difluoromethoxybiphenyl 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 40.0 g (yield 70.1%) of the trans isomer.

Workup

  1. customto obtain a Grignard's reagent

Sources & evidence

ORD record
ord-622435d1c2d346a5a2ef83fd646ca397
Source dataset
uspto-grants-1996_12
Patent number
US05582764

Reaction notes

Loading…