1-Bromo-3-methylbutane → HCID 178447723, compound

HRID 2258170Notes

Reaction equation

HRID 2258170 reaction equation
[CH3:1][CH:2]([CH3:6])[CH2:3][CH2:4]Br.[Mg].Cl[SiH:9]1[CH2:14][CH2:13][CH:12]([C:15]2[CH:20]=[CH:19][C:18]([C:21]3[CH:26]=[CH:25][C:24]([F:27])=[C:23]([F:28])[CH:22]=3)=[CH:17][CH:16]=2)[CH2:11][CH2:10]1>C1COCC1>[CH3:1][CH:2]([CH3:6])[CH2:3][CH2:4][Si@H:9]1[CH2:10][CH2:11][C@H:12]([C:15]2[CH:16]=[CH:17][C:18]([C:21]3[CH:26]=[CH:25][C:24]([F:27])=[C:23]([F:28])[CH:22]=3)=[CH:19][CH:20]=2)[CH2:13][CH2:14]1

Participants

5

Reactant 3

HCID 78911-Bromo-3-methylbutaneHCID 5462224MagnesiumHCID 1317201274'-(4-Chloro-4-silacyclohexyl)-3,4-difluorobiphenyl

Product 1

HCID 178447723HCID 178447723, compoundYield 90%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

2.5 g (20 mmol) of 3-methylbutyl bromide 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 6.5 g (21 mmol) of 4'-(4-chloro-4-silacyclohexyl)-3,4-difluorobiphenyl to obtain 4'-(trans-4-(3-methylbutyl)-4-silacyclohexyl)-3,4-difluorobiphenyl. The silacyclohexane rings of this product were a mixture of trans and cis isomers. They were separated by means of chromatography to obtain 6.5 g of the trans isomer (yield 90%). The results of its analysis are shown below.

Workup

  1. customto obtain a Grignard's reagent

Sources & evidence

ORD record
ord-6aacb21e98c144eb959226c4b45d1094
Source dataset
uspto-grants-1997_08
Patent number
US05659059

Reaction notes

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