Aniline → 2-(2-bromophenyl)thiophene

HRID 1080723Notes

Reaction equation

C(ON=O)CC(C)C.[Br:9][C:10]1[CH:16]=[CH:15][CH:14]=[CH:13][C:11]=1N.NC1C=CC=CC=1.CCCCCC.CCOCC.[S:35]1[CH:39]=[CH:38][CH:37]=[CH:36]1>>[Br:9][C:10]1[CH:16]=[CH:15][CH:14]=[CH:13][C:11]=1[C:36]1[S:35][CH:39]=[CH:38][CH:37]=1

Participants

Reactant 5

HCID 6115Aniline

HCID 8030Thiophene2×

HCID 8053Isoamyl Nitrite

HCID 119922-Bromoaniline

HCID 21584099Diethylether hexane

Product 1

HCID 27955602-(2-bromophenyl)thiopheneYield 34%

Conditions

Temperature: 90 °C

Procedure

A solution of 8.8 mL of isoamylnitrite (65.5 mmol) in 85 mL of thiophene under a nitrogen atmosphere was heated to 50° C. and treated dropwise with a solution of 7.5 g of 2-bromoaniline (43.5 mmol) dissolved in 20 mL of thiophene. After addition was complete, the temperature was raised to 90° C. After 90 minutes, no starting aniline was observed by thin layer chromatography (hexane/ether;100:5). The reaction mixture volume was reduced by atmospheric distillation. The residue was dissolved in ether and the organic layer was washed twice with water, dried over magnesium sulfate and evaporated under vacuum. The residue was dissolved in n-hexane/ether (100:5) and passed over silica gel, eluting with n-hexane/ether (100:5) to give 3.5 g (14.6 mmol, 34%) of the product, 1H NMR (200 MHz, CDCl3): 7.11 (m, 1H), 7.16 (dd, 1H), 7.27 (m, 2H), 7.37 (dd, 1H), 7.42 (dd, 1H), 7.66 (dd, 1H).

Workup

additionAfter addition
distillationThe reaction mixture volume was reduced by atmospheric distillation
dissolutionThe residue was dissolved in ether
washthe organic layer was washed twice with water
dry with materialdried over magnesium sulfate
customevaporated under vacuum
dissolutionThe residue was dissolved in n-hexane/ether (100:5)
washeluting with n-hexane/ether (100:5)

Sources & evidence

ORD record: ord-b3f26c10fbce428d93c43342f2505333
Source dataset: uspto-grants-1996_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05583130

Reaction notes

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