Selective Nitration of Aromatic Compounds with Bismuth Subnitrate and Thionyl Chloride
Abstract
:Introduction
Results and Discussion
Entry | Substrate | Product | Sub:NO3 ratio | Time h | Yield% |
1. | benzene | nitrobenzene | 1 : 1 | 6 | 87 |
2. | toluene | 2-nitrotoluene 4- nitrotoluene | 1 : 1 | 3 | 62 27 |
3. | m-xylene | 4- nitro-m-xylene | 1 : 1 | 3 | 74 |
4. | mesitylene | 2-nitromesitylene | 1 : 1 | 2 | 84 |
5. | acetanilide | 2-nitroacetanilide 4-nitroacetanilide | 1 : 1 | 3 | 16 52 |
6. | anisole | 2-nitroanisole 4-nitroanisole | 1 : 1 | 2 | 12 76 |
7. | 4-bromoanisole | 4-bromo-2-nitroanisole | 1 : 1 | 6 | 75 |
8. | 2-chloroanisole | 2-chloro-4-nitroanisole | 1 : 1 | 5 | 74 |
9. | bromobenzene | 2-bromonitrobenzene 4- bromonitrobenzene | 1 : 1 | 9 | 18 60 |
10. | chlorobenzene | 2-chloronitrobenzene 4- chloronitrobenzene | 1 : 1 | 9 | 27 49 |
Entry | Substrate | Product | Sub:NO3 ratio | Time h | Yield % |
1. | naphthalene | 1-nitronaphthalene | 1 : 1 | 2 | 68 |
2. | 2-methylnaphthalene | 1-nitro-2-methyl naphthalene | 1 : 1 | 2 | 76 |
3. | acenaphthene | 5-nitroacenaphthene | 1 : 1 | 2 | 72 |
4. | biphenylene | 2-nitrobiphenylene | 1 : 1 | 1 | 81 |
5. | fluorene | 2-nitrofluorene | 1 : 1 | 2 | 74 |
6. | phenanthrene | 9-nitrophenanthrene | 1 : 1 | 2 | 64 |
7. | pyrene | 1-nitropyrene | 1 : 1 | 1 | 75 |
8. | biphenyl | 4-nitrobiphenyl | 1 : 1 | 1 | 73 |
Entry | Substrate | Product | Sub:NO3 ratio | Time h | Yield% |
1. | phenol | 2-nitrophenol 4- nitrophenol | 1 : 1 | 0.5 | 42 46 |
2. | phenol | 2,4-dinitrophenol 2,6- dinitrophenol | 1 : 2 | 2 | 72 14 |
3. | o-cresol | 2-methyl-4-nitrophenol 2-methyl-6-nitrophenol | 1 : 1 | 0.5 | 56 28 |
4. | o-cresol | 4,6-dinitro-2-methylphenol | 1 : 2 | 2 | 83 |
5. | p- cresol | 4-methyl-2-nitrophenol | 1 : 1 | 0.5 | 86 |
6. | p- cresol | 2,6-dinitro-4-methylphenol | 1 : 2 | 1 | 82 |
7. | 2-bromophenol | 2-bromo-4-nitrophenol 2-bromo-6-nitrophenol | 1 : 1 | 1 | 52 22 |
8. | 2- bromophenol | 2-bromo-4,6-dinitrophenol | 1 : 2 | 3 | 70 |
9. | 4-chlorophenol | 4-chloro-2-nitrophenol | 1 : 1 | 1 | 78 |
10. | 4- chlorophenol | 4-chloro-2,6-dinitrophenol | 1 : 2 | 3 | 72 |
11. | salicyldehyde | 4-nitrosalicyldehyde | 1 : 1 | 3 | 63 |
12. | 4-nitrophenol | 2,4-dinitrophenol | 1 : 1 | 3 | 78 |
Experimental
General
Typical procedure
References
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Muathen, H.A. Selective Nitration of Aromatic Compounds with Bismuth Subnitrate and Thionyl Chloride. Molecules 2003, 8, 593-598. https://doi.org/10.3390/80700593
Muathen HA. Selective Nitration of Aromatic Compounds with Bismuth Subnitrate and Thionyl Chloride. Molecules. 2003; 8(7):593-598. https://doi.org/10.3390/80700593
Chicago/Turabian StyleMuathen, Hussni A. 2003. "Selective Nitration of Aromatic Compounds with Bismuth Subnitrate and Thionyl Chloride" Molecules 8, no. 7: 593-598. https://doi.org/10.3390/80700593