1-Bromopropane → HCID 178460930, compound

HRID 259875Notes

Reaction equation

HRID 259875 reaction equation
[CH3:1][CH2:2][CH2:3]Br.[Mg].Cl[Si@H:7]1[CH2:12][CH2:11][C@H:10]([CH2:13][CH2:14][C:15]2[CH:20]=[CH:19][C:18]([C:21]3[CH:26]=[CH:25][C:24]([F:27])=[CH:23][CH:22]=3)=[CH:17][CH:16]=2)[CH2:9][CH2:8]1>O1CCCC1>[CH2:3]([Si@H:7]1[CH2:12][CH2:11][C@H:10]([CH2:13][CH2:14][C:15]2[CH:20]=[CH:19][C:18]([C:21]3[CH:22]=[CH:23][C:24]([F:27])=[CH:25][CH:26]=3)=[CH:17][CH:16]=2)[CH2:9][CH2:8]1)[CH2:2][CH3:1]

Participants

5

Reactant 3

HCID 78401-BromopropaneHCID 5462224MagnesiumHCID 178505504HCID 178505504, compound

Product 1

HCID 178460930HCID 178460930, compoundYield 90%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent3×

Procedure

2.5 g (20 mmol) of n-propyl bromide was dripped into a mixture of 0.5 g (21 mmol) of magnesium and 50 ml of tetrahydrofuran (hereafter abbreviated as "THF") to obtain a Grignard's reagent. This solution was then dripped into a 50 ml THF solution of 6.7 g (20 mmol) of 4-[2-(trans-4-chloro-4-silacyclohexyl)ethyl]-4'-fluorobiphenyl to obtain 4-[2-(trans-4-n-propyl-4-silacyclohexyl) ethyl]-4'-fluorobiphenyl. The silacyclohexane rings of this product were a mixture of trans isomers and cis isomers. After a conventional after treatment, they were separated by means of chromatography to obtain 6.1 g of the trans isomers (yield 90%).

Workup

  1. customto obtain a Grignard's reagent

Sources & evidence

ORD record
ord-a7838876b0f74e919cd1b1f1b86bc187
Source dataset
uspto-grants-1996_06
Patent number
US05523440

Reaction notes

Loading…