1-Bromopentane → HCID 178447733, compound

HRID 2258173Notes

Reaction equation

HRID 2258173 reaction equation
[CH2:1](Br)[CH2:2][CH2:3][CH2:4][CH3:5].[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]=[C:25]([F:27])[C:24]([O:28][CH:29]([F:31])[F:30])=[C:23]([F:32])[CH:22]=3)=[CH:17][CH:16]=2)[CH2:11][CH2:10]1>C1COCC1>[CH2:1]([Si@H:9]1[CH2:14][CH2:13][C@H:12]([C:15]2[CH:20]=[CH:19][C:18]([C:21]3[CH:22]=[C:23]([F:32])[C:24]([O:28][CH:29]([F:31])[F:30])=[C:25]([F:27])[CH:26]=3)=[CH:17][CH:16]=2)[CH2:11][CH2:10]1)[CH2:2][CH2:3][CH2:4][CH3:5]

Participants

5

Reactant 3

HCID 80571-BromopentaneHCID 5462224MagnesiumHCID 123417679HCID 123417679, compound

Product 1

HCID 178447733HCID 178447733, compoundYield 82%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

3.0 g (20 mmol) of n-pentyl 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 7.8 g (20 mmol) of 4'-(4-chloro-4-silacyclohexyl)-3,5-difluoro-4-difluoromethoxybiphenyl to obtain 4'-(trans-4-n-pentyl-4-silacyclohexyl)-3,5-difluoro-4-difluoromethoxybiphenyl. The silacyclohexane rings of this product were a mixture of trans and cis isomers. They were separated by means of chromatography to obtain 6.6 g of the trans isomer (yield 82%).

Workup

  1. customto obtain a Grignard's reagent

Sources & evidence

ORD record
ord-1da27a402c2f49f79c49f54eb6cadc1a
Source dataset
uspto-grants-1997_08
Patent number
US05659059

Reaction notes

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