1-Bromopentane → HCID 178447739, compound

HRID 2258168Notes

Reaction equation

HRID 2258168 reaction equation
[CH2:1](Br)[CH2:2][CH2:3][CH2:4][CH3:5].[Mg].C(O[SiH:11]1[CH2:16][CH2:15][CH:14]([C:17]2[C:22]([F:23])=[CH:21][C:20]([C:24]3[CH:29]=[CH:28][C:27]([O:30][C:31]([F:34])([F:33])[F:32])=[CH:26][CH:25]=3)=[C:19]([F:35])[CH:18]=2)[CH2:13][CH2:12]1)C>C1COCC1>[CH2:1]([Si@H:11]1[CH2:16][CH2:15][C@H:14]([C:17]2[C:22]([F:23])=[CH:21][C:20]([C:24]3[CH:25]=[CH:26][C:27]([O:30][C:31]([F:34])([F:32])[F:33])=[CH:28][CH:29]=3)=[C:19]([F:35])[CH:18]=2)[CH2:13][CH2:12]1)[CH2:2][CH2:3][CH2:4][CH3:5]

Participants

5

Reactant 3

HCID 80571-BromopentaneHCID 5462224MagnesiumHCID 131720126HCID 131720126, compound

Product 1

HCID 178447739HCID 178447739, compoundYield 85%

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 8.8 g (20 mmol) of 4'-(4-ethoxy-4-silacyclohexyl)-2',5'-difluoro-4-trifluoromethoxybiphenyl to obtain 4'-(trans-4-n-pentyl-4-silacyclohexyl)-2',5'-difluoro-4-trifluoromethoxybiphenyl. The silacyclohexane rings of this product were a mixture of trans and cis isomers. They were separated by means of chromatography to obtain 7.5 g of the trans isomer (yield 85%).

Workup

  1. customto obtain a Grignard's reagent

Sources & evidence

ORD record
ord-2b7eb72f13d24db6a2013c821b8e4db1
Source dataset
uspto-grants-1997_08
Patent number
US05659059

Reaction notes

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