1-Bromopropane → HCID 178460920, compound

HRID 2258166Notes

Reaction equation

HRID 2258166 reaction equation
[CH3:1][CH2:2][CH2:3]Br.[Mg].F[SiH:7]1[CH2:12][CH2:11][CH:10]([C:13]2[CH:18]=[CH:17][C:16]([C:19]3[CH:24]=[C:23]([F:25])[C:22]([F:26])=[C:21]([F:27])[CH:20]=3)=[CH:15][CH:14]=2)[CH2:9][CH2:8]1>C1COCC1>[CH2:3]([Si@H:7]1[CH2:12][CH2:11][C@H:10]([C:13]2[CH:14]=[CH:15][C:16]([C:19]3[CH:20]=[C:21]([F:27])[C:22]([F:26])=[C:23]([F:25])[CH:24]=3)=[CH:17][CH:18]=2)[CH2:9][CH2:8]1)[CH2:2][CH3:1]

Participants

5

Reactant 3

HCID 78401-BromopropaneHCID 5462224MagnesiumHCID 123322905HCID 123322905, compound

Product 1

HCID 178460920HCID 178460920, compoundYield 91%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

2.5 g (20 mmol) of n-propyl 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 (20 mmol) of 4'-(4-fluoro-4-silacyclohexyl)-3,4,5-trifluorobiphenyl to obtain 4'-(trans-4-n-propyl-4-silacyclohexyl)-3,4,5-trifluorobiphenyl. The silacyclohexane rings of this product were a mixture of trans and cis isomers. They were separated by means of chromatography to obtain 5.9 g of the trans isomer (yield 91%).

Workup

  1. customto obtain a Grignard's reagent

Sources & evidence

ORD record
ord-eb6f9da4216b402ebb4cdf6d409c8878
Source dataset
uspto-grants-1997_08
Patent number
US05659059

Reaction notes

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