ChemicalBook CAS DataBase List 5-Bromo-1,3-difluoro-2-nitrobenzene

5-Bromo-1,3-difluoro-2-nitrobenzene synthesis

3synthesis methods

Product Name:5-Bromo-1,3-difluoro-2-nitrobenzene
CAS Number:147808-42-2
Molecular formula:C6H2BrF2NO2
Molecular Weight:237.99

Sodium perborate tetrahydrate (18.5 g, 0.12 mol, 5.0 eq) was suspended in glacial acetic acid (125 mL) and heated to 65 °C. 4-Bromo-2,6-difluoroanilline(5.0 g, 24.0 mmol, 1.0 eq) dissolved in glacial acetic acid (50 mL) was added slowly through a funnel over 4 h. After the addition, the reaction mixture was heated for 3 h additional hours before a second portion of NaBO3·4H2O (6.0 g, 30.0 mmol) was added. Then, the mixture was stirred for 14 h, and a third portion of oxidating agent (9.0 g, 45.0 mmol) was added. 9 h after the third addition full consumption of the starting material was indicated by TLC. After cooling the mixture to room temperature, the formed solid was removed by filtration. The filtrate was poured into ice-cold water (300 mL). The precipitated solid was filtered off and dried to give the product 5-Bromo-1,3-difluoro-2-nitrobenzene as a yellow solid (3.40 g 60percent).

67567-26-4 Synthesis

67567-26-4
339 suppliers
$5.00/1g

147808-42-2
168 suppliers
$5.00/250mg

Yield:147808-42-2 68%

Reaction Conditions:

Stage #1:4-bromo-2,6-difluoroaniline with sodium perborate in acetic acid at 65 - 70; for 72 h;Heating / reflux;
Stage #2: with water at 0;

Steps:

24
To a suspension of sodium perborate tetrahydrate (1.78 mmol, 0.27 g) in 10 ml of acetic acid stirred at 65⁰C was added a solution of (4-bromo-2,6-difluorophenyl)amine (1.78 mmol, 0.42 g, 1 eq.) in 5 ml of acetic acid over one hour dropwise. The reaction was heated at 65⁰C over 3 days. Sodium perborate tetrahydrate (2 eq., 3.56 mmol, 0.54 g) was added again. After 3 hours, sodium perborate tetrahydrate (1eq., 1.78 mmol, 0.27 g) was added again. Additional sodium perborate tetrahydrate (3eq., 5.34 mmol, 0.81 g) was again added. The reaction was then left overnight at 7O⁰C under reflux and under argon. The solution was then cooled to room temperature and poured onto ice and extracted with ethyl acetate (2x). The combined organics were washed with water and brine. The organics were dried over MgSO₄, filtered and the organic solvent was removed under reduced pressure to afford the crude product which was purified by silica chromatography (ethyl acetate-4% n-hexane 96%) to afford the title compound, 0.29 g, 68%. ¹H NMR δ (d⁶DMSO, 400MHz): 7.964 (2H, d)

References:

GLAXO GROUP LIMITED WO2007/36715, 2007, A2 Location in patent:Page/Page column 51

FullText

122129-79-7
51 suppliers
inquiry

147808-42-2
168 suppliers
$5.00/250mg

References

5509-65-9
470 suppliers
$10.00/10g

147808-42-2
168 suppliers
$5.00/250mg

References

5-Bromo-1,3-difluoro-2-nitrobenzene Related Search:

4-Bromobenzotrifluoride 2-broMo-1-ethyl-4-nitrobenzene 4-Fluoronitrobenzene 1,3-Dinitrobenzene