1-Bromo-4-fluorobutane → HCID 178506029, compound

HRID 2258174Notes

Reaction equation

HRID 2258174 reaction equation
[F:1][CH2:2][CH2:3][CH2:4][CH2:5]Br.[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]=[CH:25][C:24]([O:27][C:28]([F:31])([F:30])[F:29])=[CH:23][CH:22]=3)=[CH:17][CH:16]=2)[CH2:11][CH2:10]1>C1COCC1>[F:1][CH2:2][CH2:3][CH2:4][CH2:5][Si@H:9]1[CH2:14][CH2:13][C@H:12]([C:15]2[CH:16]=[CH:17][C:18]([C:21]3[CH:26]=[CH:25][C:24]([O:27][C:28]([F:29])([F:30])[F:31])=[CH:23][CH:22]=3)=[CH:19][CH:20]=2)[CH2:11][CH2:10]1

Participants

5

Reactant 3

HCID 100221-Bromo-4-fluorobutaneHCID 5462224MagnesiumHCID 1234736194'-(4-Chloro-4-silacyclohexyl)-4-trifluoromethoxybiphenyl

Product 1

HCID 178506029HCID 178506029, compoundYield 71%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

3.1 g (20 mmol) of fluorobutyl 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 7.4 g (20 mmol) of 4'-(4-chloro-4-silacyclohexyl)-4-trifluoromethoxybiphenyl to obtain 4'-(trans-4-(4-fluorobutyl)-4-silacyclohexyl)-4-trifluoromethoxybiphenyl. The silacyclohexane rings of this product were a mixture of trans isomers and cis isomers. They were separated by means of chromatography to obtain 5.8 g of the trans isomers (yield 71%).

Workup

  1. customto obtain a Grignard's reagent

Sources & evidence

ORD record
ord-42c6c434904b4d0dbfbcd4a4e2dce5a9
Source dataset
uspto-grants-1997_08
Patent number
US05659059

Reaction notes

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