1-Bromopentane → HCID 178447745, compound

HRID 1901415Notes

Reaction equation

HRID 1901415 reaction equation
[CH2:1](Br)[CH2:2][CH2:3][CH2:4][CH3:5].[Mg].Cl[SiH:9]1[CH2:14][CH2:13][CH:12]([CH2:15][CH2:16][C:17]2[CH:22]=[CH:21][C:20]([C:23]3[CH:28]=[CH:27][C:26]([C:29]4[CH:34]=[CH:33][C:32]([F:35])=[CH:31][CH:30]=4)=[CH:25][CH:24]=3)=[CH:19][CH:18]=2)[CH2:11][CH2:10]1>O1CCCC1>[CH2:1]([Si@H:9]1[CH2:14][CH2:13][C@H:12]([CH2:15][CH2:16][C:17]2[CH:22]=[CH:21][C:20]([C:23]3[CH:28]=[CH:27][C:26]([C:29]4[CH:30]=[CH:31][C:32]([F:35])=[CH:33][CH:34]=4)=[CH:25][CH:24]=3)=[CH:19][CH:18]=2)[CH2:11][CH2:10]1)[CH2:2][CH2:3][CH2:4][CH3:5]

Participants

5

Reactant 3

HCID 80571-BromopentaneHCID 5462224MagnesiumHCID 123201913HCID 123201913, compound

Product 1

HCID 178447745HCID 178447745, compoundYield 93%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent3×

Procedure

15.1 g (100 mmol) of n-pentyl bromide was dripped into a mixture of 2.4 g of magnesium (100 mmol) and 60 ml of tetrahydrofuran (hereafter referred to as "THF") to obtain a Grignard's reagent. This solution was then dripped into a 300 ml THF solution of 40.9 g of 4-(2-(4-chloro-4-silacyclohexyl)ethyl)-4'-(4-fluorophenyl)biphenyl. The reaction mixture thus obtained was a mixture of trans isomers and cis isomers with respect to the silacyclohexane ring. After a conventional after treatment, they were separated by means of chromatography to obtain 38.1 g (yield 93%) of the target product.

Workup

  1. customto obtain a Grignard's reagent
  2. customThe reaction mixture thus obtained
  3. additiona mixture of trans isomers and cis isomers with respect to the silacyclohexane ring
  4. customAfter a conventional after treatment, they were separated by means of chromatography

Sources & evidence

ORD record
ord-c7943a8a3a294c74a57d9f44abd020fd
Source dataset
uspto-grants-1996_11
Patent number
US05578244

Reaction notes

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