3-Bromothiophene → HCID 54264487, compound

HRID 1276104Notes

Reaction equation

HRID 1276104 reaction equation
[S:1]1[CH:5]=[CH:4][C:3]([Li])=[CH:2]1.BrC1C=CSC=1.C([Li])CCC.[Cl:18][CH2:19][CH2:20][CH2:21][CH2:22]I.C(=O)=O.CC(C)=O>>[S:1]1[CH:5]=[CH:4][C:3]([CH2:22][CH2:21][CH2:20][CH2:19][Cl:18])=[CH:2]1

Participants

6

Reactant 5

HCID 133833-BromothiopheneHCID 825271-Chloro-4-iodobutaneHCID 18522661Acetone cardiceHCID 178418339ButyllithiumHCID 178506756HCID 178506756, compound2×

Product 1

HCID 54264487HCID 54264487, compound

Procedure

3-Thienyl lithium was generated from 3-bromothiophene and n-butyl lithium at -70° C. To the 3-thienyl lithium was then added an excess of 1-chloro-4-iodobutane at dry ice-acetone temperature. Upon slow warm up to room temperature a mixture of 2 and 3-thienyl butylchloride were obtained. The mixture was converted to the 2- and 3-thienyl butyl amines via the azide intermediates (Scheme 9) as described for the synthesis of 2-thienyl butyl amine, then reacted with thiophosgene to give the desired product, 3-TBITC, in low yield. The 2 isomers were separated by preparative liquid chromatography using a recycling mode. The 3-TBITC was obtained in 97% purity.

Workup

  1. additiona mixture of 2

Sources & evidence

ORD record
ord-ce50a1176fe94491a635d9673f9c7870
Source dataset
uspto-grants-2000_12
Patent number
US06166003

Reaction notes

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