1-Octyne → 3-Bromo-2-(1-octynyl)thiophene

HRID 569496

Reaction equation

Br[C:2]1[S:3][CH:4]=[CH:5][C:6]=1[Br:7].[CH:8]#[C:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH3:15]>>[Br:7][C:6]1[CH:5]=[CH:4][S:3][C:2]=1[C:8]#[C:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH3:15]

Participants

Reactant 2

HCID 123701-Octyne

HCID 765902,3-Dibromothiophene

Product 1

HCID 201471663-Bromo-2-(1-octynyl)thiopheneYield 87.5%

Procedure

2,3-Dibromothiophene (3.78 g 15.6 mmole) was reacted with 1-octyne (2.57 g 23.4 mmole) using the method given in Example 20. The reaction product was purified by chromatography on silica eluting with hexane to yield 3.70 g (87.2%) of the title compound as a yellow oil bp 0.05 155°, νmax (mull) 3100, 2225, 870, 710; δ(CDCl3), 0.9(3H, t, J=6 Hz), 1.3(8H, m), 2.47(2H, t, J=6 Hz), 6.9(d, 1H, J=9 Hz), 7.13(1H, d, J=9 Hz).

Workup

customThe reaction product was purified by chromatography on silica eluting with hexane

Sources & evidence

ORD record: ord-a5f674a2683a40f19ec3951d1efc41b4
Source dataset: uspto-grants-1988_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04732901

Linked notes

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