ChemicalBook CAS DataBase List 5-BROMO-6-BROMOMETHYL-1 3-BENZODIOXOLE

5-BROMO-6-BROMOMETHYL-1 3-BENZODIOXOLE synthesis

5synthesis methods

Product Name:5-BROMO-6-BROMOMETHYL-1 3-BENZODIOXOLE
CAS Number:5434-47-9
Molecular formula:C8H6Br2O2
Molecular Weight:293.94

120-57-0 Synthesis

120-57-0
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5434-47-9
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$40.00/1g

Yield:5434-47-9 100%

Reaction Conditions:

with bromine at 60; for 12 h;

Steps:

304.a Example 304; 4-[3-(6-methyl-benzo[1,3]dioxol-5-yl)-benzenesulfonyl]-5-methylsulfanyl-thiophene-2-carboxamidine trifluoroacetate; a); 5-Bromo-6-methyl-benzo[1,3] dioxole

Bromine (3.36 g, 21 mmol) was added to a solution of piperonal alcohol (3.0 g, 20 mmol) in chloroform (15 mL). The solution was heated to 60 oC FOR 12 h. After cooling, DCM (60 mL) was added and the solution was extracted with aq NAHC03 (2 x 20 mL), brine (20 mL), and was dried over sodium sulfate. After concentration, the residue 5-bromo-6-bromomethyl-benzo[1,3] dioxole (5. 88G, 100%), solidified upon standing. A portion of the crude solid (2.44g, 8. 33 mmol) was dissolved in THF and cooled TO-78 oC. Lithium aluminum hydride (348 mg, 9.16 mmol) was added and the solution was stirred for 3 h. An additional portion of LAH (80 mg, 2.03 mmol) was added and the reaction was stirred an additional hour. EtOAc was added carefully to quench the excess LAH, followed by addition OF MEOH (20 mL). The salts were filtered and the filtrate was concentrated in vacuo, to yield the title compound (1.76 g, 99%) which was used without further purification. 1H-NMR (CDC13) : δ 7.01 (s, 1H), 6.73 (s, 1H), 5.95 (s, 2H), 2.32 (s, 3H).

References:

WO2003/99805,2003,A1 Location in patent:Page 418-419

495-76-1 Synthesis