ChemicalBook CAS DataBase List 4-Bromoquinoline

4-Bromoquinoline synthesis

11synthesis methods

Product Name:4-Bromoquinoline
CAS Number:3964-04-3
Molecular formula:C9H6BrN
Molecular Weight:208.05

611-36-9 Synthesis

611-36-9
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$8.00/5g

3964-04-3
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$26.39/1g

Yield:3964-04-3 88%

Reaction Conditions:

with phosphorus tribromide in N,N-dimethyl-formamide; for 0.666667 h;Inert atmosphere;

Steps:

1.1 Example 1 - Synthesis of Compound 1 (4-Phenylethynyl-quinoline)

Step 1 : To a stirred solution of quinolin-4-ol (4.00 g, 27.6 mmol) in dry DMF (30 mL) was added phosphorus tribromide (7.61 g, 28.2 mmol) dropwise for 10 min. The reddish colored suspension was stirred for 30 min under nitrogen atmosphere. After complete consumption of starting material, the reaction mixture was quenched with ice, stirred for anther 30 min, then basified to pH -10 with a solution of saturated sodium bicarbonate (20 mL). The reaction mixture was extracted with ethyl acetate (2 x 100 mL) and the combined organic phase was dried over anhydrous sodium sulfate, filtered and evaporated in vacuo. The residue was purified on silica gel column using dichloromethane / methanol (0% to 10%) as eluent to give 4-bromo- quinoline (5.04 g; 88%) as a yellow solid; LCMS (ESI) 208 (M+H); H NMR (400 MHz, CHLOROFORM-d) δ ppm: 8.69 (d, J=4.69 Hz, 1 H), 8.20 (dd, J=8 39, 0.88 Hz, 1 H), 8.08 - 8.16 (m, 1 H), 7.78 (ddd, J=8.39, 6.98, 1 .37 Hz, 1 H), 7.71 (d, J=4.69 Hz, 1 H), 7.66 (ddd, J=8.31 , 7.04, 1.15 Hz, 1 H).

References:

WO2014/121883,2014,A1 Location in patent:Page/Page column 51