ChemicalBook CAS DataBase List 1-Bromoisoquinoline

1-Bromoisoquinoline synthesis

6synthesis methods

Product Name:1-Bromoisoquinoline
CAS Number:1532-71-4
Molecular formula:C9H6BrN
Molecular Weight:208.05

1532-72-5

1532-71-4

General method: To a stirred solution of isoquinoline-N-oxide (0.1 M in anhydrous CH2Cl2), POBr3 (1.2 eq.) was slowly added under argon protection at 0 °C, followed by dropwise addition of DMF (0.5 eq.). The reaction mixture was gradually warmed to 25 °C and stirred continuously until the reaction was complete (monitored by TLC). Upon completion of the reaction, saturated aqueous sodium carbonate solution was slowly added and the pH was adjusted to 7-8. The organic and aqueous phases were separated and the aqueous phase was fully extracted with CH2Cl2. All organic phases were combined, washed with brine, dried with anhydrous Na2SO4, filtered and concentrated under reduced pressure to obtain the crude product. The crude product was purified by fast column chromatography with the eluent of petroleum ether/ethyl acetate (100:1).

1532-72-5
171 suppliers
$15.00/1g

1532-71-4
206 suppliers
$9.00/100mg

Yield:1532-71-4 55%

Reaction Conditions:

with N,N-dimethyl-formamide;phosphorus(V) oxybromide in dichloromethane at 0 - 25; for 6 h;Inert atmosphere;regioselective reaction;

Steps:

11 4.2. General procedure I for the bromination of azine N-oxides
General procedure: To a stirred solution of the appropriate azine N-oxides in anhydrous CH₂Cl₂ (0.1 M) at 0 °C is added POBr₃ (1.2 equiv) followed by dropwise addition of DMF (0.5 equiv) under argon. The resulting reaction mixture was warmed to 25 °C and stirred for several hours until the reaction is complete as indicated by TLC. Saturated aqueous sodium carbonate solution is added to the reaction mixture slowly to adjust the pH to 7-8. The resulting mixture is separated and the aqueous phase is extracted with CH₂Cl₂ thoroughly. The organic phase is combined and washed with brine, dried over Na₂SO₄, filtered and concentrated under reduced pressure to afford the crude product, which is purified by flash column chromatography using PE/EA (100:1) as eluent.

References:

Wang, Dong;Wang, Yuxi;Zhao, Junjie;Li, Linna;Miao, Longfei;Wang, Dong;Sun, Hua;Yu, Peng [Tetrahedron,2016,vol. 72,# 38,p. 5762 - 5768]

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