1-Bromopentane → HCID 178447726, compound

HRID 2258167Notes

Reaction equation

HRID 2258167 reaction equation
[CH2:1](Br)[CH2:2][CH2:3][CH2:4][CH3:5].[Mg].CO[SiH:10]1[CH2:15][CH2:14][CH:13]([C:16]2[CH:21]=[CH:20][C:19]([C:22]3[CH:27]=[CH:26][C:25]([O:28][CH2:29][CH2:30][CH3:31])=[CH:24][C:23]=3[F:32])=[C:18]([F:33])[CH:17]=2)[CH2:12][CH2:11]1>C1COCC1>[CH2:1]([Si@H:10]1[CH2:15][CH2:14][C@H:13]([C:16]2[CH:21]=[CH:20][C:19]([C:22]3[CH:27]=[CH:26][C:25]([O:28][CH2:29][CH2:30][CH3:31])=[CH:24][C:23]=3[F:32])=[C:18]([F:33])[CH:17]=2)[CH2:12][CH2:11]1)[CH2:2][CH2:3][CH2:4][CH3:5]

Participants

5

Reactant 3

HCID 80571-BromopentaneHCID 5462224MagnesiumHCID 131720125HCID 131720125, compound

Product 1

HCID 178447726HCID 178447726, compoundYield 86%

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 7.5 g (20 mmol) of 4'-(4-methoxy-4-silacyclohexyl)-2,2'-difluoro-4-propoxybiphenyl to obtain 4'-(trans-4-n-pentyl-4-silacyclohexyl)-2, 2'-difluoro-4-propoxybiphenyl. The silacyclohexane rings of this product were a mixture of trans and cis isomers. They were separated by means of chromatography to obtain 7.1 g of the trans isomer (yield 86%).

Workup

  1. customto obtain a Grignard's reagent

Sources & evidence

ORD record
ord-18e20e08a0124f549f2f8ddc4033378a
Source dataset
uspto-grants-1997_08
Patent number
US05659059

Reaction notes

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