1,4-Dibromobutane → 1-(4-Bromo-2-tert-butyl-phenyl)-pyrrolidine

HRID 1698403Notes

Reaction equation

[Br:1][C:2]1[CH:7]=[CH:6][C:5]([NH2:8])=[C:4]([C:9]([CH3:12])([CH3:11])[CH3:10])[CH:3]=1.[H-].[Na+].Br[CH2:16][CH2:17][CH2:18][CH2:19]Br>>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[CH2:19][CH2:18][CH2:17][CH2:16]2)=[C:4]([C:9]([CH3:12])([CH3:11])[CH3:10])[CH:3]=1

Participants

Reactant 3

HCID 80561,4-Dibromobutane

HCID 24758Sodium hydride

HCID 119590004-bromo-2-tert-butylphenylamine

Product 1

HCID 666722611-(4-Bromo-2-tert-butyl-phenyl)-pyrrolidineYield 61.2%

Procedure

In a manner analogous to example 1 b, the process is carried out by a reaction of 10 g (44 mmol) of 4-bromo-2-tert-butylphenylamine with 3.8 g (96 mmol) of 60% sodium hydride and with 3.4 ml (96 mmol) of 1,4-dibromobutane. 7.6 g of 1-(4-bromo-2-tert-butylphenyl)-pyrrolidine are obtained in the form of an oil (yield=61%).

Sources & evidence

ORD record: ord-dab554a2275f4709aa55977e66c0f311
Source dataset: uspto-grants-2012_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08163952B2

Reaction notes

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