4-Bromo-3-nitroanisole

The cyclization of IV-allyl-o-haloanilines was adapted to the solid phase for both indoles [332, 333] and oxindoles [334]. For example, as illustrated below, a library of l-acyl-3-aIkyl-6-hydroxyindoles is readily assembled from acid chlorides, allylic bromides, and 4-bromo-3-nitroanisole [332], Zhang and Maryanoff used the Rink amide resin to prepare Af-benzylindole-3-acetamides and related indoles via Heck cyclization [333], and Balasubramanian employed this technology to the synthesis of oxindoles via the palladium cyclization of o-iodo-N-acryloylanilines [334], This latter cyclization route to oxindoles is presented later in this section. 

C7H6BrN03 4-bromo-3-nitroanisole 5344-78-5 25.00 1.7038 2 10332 C7H6IN02 4-iodo-3-nitrotoluene 5326-39-6 25.00 1.8886 2... 

MeeOter 4-bromo-3-nitroanisole. C gO NBr. MW, 232. Yellow needles firom EtOH. M.p. 32°. Volatile in steam. 

The chemistry of indium metal is the subject of current investigation, especially since the reactions induced by it can be performed in aqueous solution.15 The selective reductions of ethyl 4-nitrobenzoate (entry 1), 2-nitrobenzyl alcohol (entry 2), l-bromo-4-nitrobenzene (entry 3), 4-nitrocinnamyl alcohol (entry 4), 4-nitrobenzonitrile (entry 5), 4-nitrobenzamide (entry 6), 4-nitroanisole (entry 7), and 2-nitrofluorenone (entry 8) with indium metal in the presence of ammonium chloride using aqueous ethanol were performed and the corresponding amines were produced in good yield. These results indicate a useful selectivity in the reduction procedure. For example, ester, nitrile, bromo, amide, benzylic ketone, benzylic alcohol, aromatic ether, and unsaturated bonds remained unaffected during this transformation. Many of the previous methods produce a mixture of compounds. Other metals like zinc, tin, and iron usually require acid-catalysts for the activation process, with resultant problems of waste disposal. 

Reversing the order of the steps used in part (b) yields 4-bromo-2-nitroanisole. 

C7H6Br2 1 -bromo-2-(bromomethyl)benzene 3433-80-5 22.00 1,8203 2 10334 C7H6IN03 3-iodo-4-nitroanisole 114279-40- 25.00 1.9259 2... 

C8H9BrO 4-bromo-3,5-dimethyl phenol 7463-51-6 23 23 1,4369 2 13757 C8H9N03 3-methyl-2-nitroanisole 5345-42-6 38.00 1.1820 2... 

Pale yellow needles. M.p. 68° ifeeOTer 6>bromo-2-nitroanisole. C HfOgNBr. MW, 232. Leaflets. M.p. 67 ... 

Wang has synthesized boronic acids derived from nitrophenols such as 45 and 46 with possible use as a recognition and signalling unit for the construction of polyboronic add sensors [21]. Synthesis of boronic acid 45 involves crossboronate ester and deprotection of the methoxy group, whereas the dinitrophenyl boronic acid 46 is prepared by nitration of 2-methoxyboronic acid and subsequent cleavage of the methoxy ether with BBtj. The resulting functionalized boronic acids are both obtained in 90% yield (Scheme 3.15). 

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