ChemicalBook CAS DataBase List Methyl 5-broMo-3-(2,2,2-trifluoroacetaMido)thiophe

Methyl 5-broMo-3-(2,2,2-trifluoroacetaMido)thiophe synthesis

4synthesis methods

Product Name:Methyl 5-broMo-3-(2,2,2-trifluoroacetaMido)thiophe
CAS Number:852330-31-5
Molecular formula:C8H5BrF3NO3S
Molecular Weight:332.09

79128-68-0 Synthesis

3-(2,2,2-trifluoro-acetylaMino)-thiophene-2-carboxylicacidMethylester

79128-68-0
46 suppliers
$17.00/1g

Methyl 5-broMo-3-(2,2,2-trifluoroacetaMido)thiophe

852330-31-5
17 suppliers
$375.72/1g

Yield:852330-31-5 48%

Reaction Conditions:

with bromine;acetic acid at 0 - 70; for 96 h;

Steps:

Methyl 5-bromo-3-(2,2,2-trifluoroacetamido)thiophene-2-carboxylate (3)

To a suspension of compound 2 (80.0 g, 319 mmol) in acetic acid (200 mL) was slowly added bromine (163 mL, 3.19 mol) at 0 °C and the mixture was stirred at 70 °C for 4 days. The reaction mixture was cooled to room temperature and partitioned between saturated aqueous Na₂SO₃ solution and DCM. The organic layer was dried over MgSO₄ and concentrated in vacuo. The residue was chromatographed on a silica gel column with a mixture of n-hexane and ethyl acetate (30:1) to give the desired product 3 (49.7g, 48%). ¹H NMR (400 MHz, CDCl₃): δ 11.15 (br s, 1H), 8.11 (s, 1H), 3.92 (s, 3H) ppm; MS (ESI): m/z: 332 [M+H⁺].

References:

Ahn, Seohyeon;Jeon, Moon-Kook [Tetrahedron,2021,vol. 91,art. no. 132247]