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ChemicalBook CAS DataBase List 1-Bromonaphthalene
90-11-9

1-Bromonaphthalene synthesis

11synthesis methods
1-Bromonaphthalene is synthesized by the reaction of naphthalene with bromine: C10H8+ Br2→ C10H7Br + HBr.
Reaction: add carbon tetrachloride and naphthalene in the reaction pot, stirring and heating, and slowly add bromine at 45℃. After adding, keep the reaction at 70-80℃ for 3-4h. distillation to recover carbon tetrachloride, wash the reaction product, distill under reduced pressure, wash again, filter, dry and get the finished product.
-

Yield:90-11-9 90%

Reaction Conditions:

with pyridinium hydrobromide perbromide in tetrahydrofuran;water at 20; for 0.333333 h;chemoselective reaction;

Steps:

4.2. Typical procedure for bromodeboronation reactions

General procedure: The trifluoroborate (1.0 mmol) was dissolved in (1:1 v/v) mixture of tetrahydrofuran and water (10 mL). Pyridinium tribromide (or tetrabutylammonium tribromide) (1.0 mmol) was added to this solution. The mixture was stirred for the appropriate time and temperature (Tables 1and 2) and then diluted with 10 mL of ether. The aqueous layer was extracted twice with ether (5 mL) and the combined organic phase was dried over anhydrous Na2SO4. After evaporation of the solvent the residue was purified by silica gel column chromatography [elute: hexane (or pentane)-ethyl acetate (or Et2O)].

References:

Yao, Min-Liang;Kabalka, George W.;Blevins, David W.;Reddy, Marepally Srinivasa;Yong, Li [Tetrahedron,2012,vol. 68,# 19,p. 3738 - 3743] Location in patent:experimental part

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