1-Bromo-3-chloropropane → 4-(4-Chlorobutyl)pyridine--hydrogen chloride (1/1)

HRID 1591281Notes

Reaction equation

HRID 1591281 reaction equation
[N:1]1[CH:6]=[CH:5][C:4]([CH2:7][Li])=[CH:3][CH:2]=1.Br[CH2:10][CH2:11][CH2:12][Cl:13]>>[ClH:13].[N:1]1[CH:6]=[CH:5][C:4]([CH2:7][CH2:10][CH2:11][CH2:12][Cl:13])=[CH:3][CH:2]=1

Participants

3

Reactant 2

HCID 80061-Bromo-3-chloropropaneHCID 178506854HCID 178506854, compound2×

Product 1

HCID 197667574-(4-Chlorobutyl)pyridine--hydrogen chloride (1/1)

Procedure

The reaction of 4-picolyllithium and 3-bromo-1-chloropropane was exothermic. It was extremely critical to keep internal temperature less than -65° C. to avoid the reaction of the desired product with 4-picolyllithium to give 1,5-bis-(4-pyridinyl)-pentane. The addition took about 2 h.

Workup

  1. customtemperature less than -65° C.

Sources & evidence

ORD record
ord-8f98fdda598542a98b1cd5aba72c50e9
Source dataset
uspto-grants-1993_04
Patent number
US05206373

Reaction notes

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