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CAS No. : | 52414-97-8 | MDL No. : | MFCD02673631 |
Formula : | C7H6BrNO2 | Boiling Point : | No data available |
Linear Structure Formula : | - | InChI Key : | XDKMDDOCVPNVMB-UHFFFAOYSA-N |
M.W : | 216.03 | Pubchem ID : | 142929 |
Synonyms : |
|
Signal Word: | Warning | Class: | |
Precautionary Statements: | P261-P280-P305+P351+P338 | UN#: | |
Hazard Statements: | H302-H312-H315-H319-H332-H335 | Packing Group: | |
GHS Pictogram: |
* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
42% | A mixture of tellurium (21.6 g, 169.4 mmol) and NaBH4 (15.0 g, 396 mmol) in 575 mL of absolute EtOH was heated at reflux under an atmosphere of N2 for 1 hr, then allowed to cool to rt. A solution of 3-bromo-2-nitrotoluene (1c; 7.32 g, 33.8 mmol) in 25 mL EtOH was added all at once and the mixture stirred at room temp for 2 hrs. The reaction mixture was filtered through a CELITE pad and the filtrate evaporated under reduced pressure. The residue was taken up in Et2O (about 200 mL), washed with brine then dried over MgSO4. Evaporation of the solvent afforded 2.66 g (42%) of 2a as a dark liquid. | |
42% | step 2 2-BROMO-6-METHYLANILINE (2a) -A mixture of tellurium (21.6 g, 169.4 mmol) and NaBH4 (15.0 g, 396 mmol) in 575 mL of absolute ETOH was heated at reflux under an atmosphere of N2 for 1 hr, then allowed to cool to rt. A solution of 3-bromo-2- nitrotoluene (LC ; 7.32g, 33.8 mmol) in 25 mL ETOH was added all at once and the mixture allowed to stir at room temperature for 2 hrs. The reaction mixture was filtered through a CELITE (D pad and the filtrate evaporated under reduced pressure. The residue was taken up in ET20 (about 200 mL), washed with brine then dried over MGS04. Evaporation of the solvent afforded 2.66g (42%) of 2a as a dark liquid. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
EXAMPLE 4 2-Bromo-6-methylbenzenamine A mixture of mercuric acetate (100 g, 0.31 mol) and 4-nitrotoluene (500 g, 3.6 mol) is heated at 150 C. for 4 hr. A small amount of precipitate is filtered off and a saturated salt solution is added. The reaction is steam distilled to remove unreacted 4-nitrotoluene (about 350 ml). A gold colored precipitate is filtered off (100 g), crushed to a fine powder and added portionwise to bromine (50 g) in a cold saturated solution of potassium bromide (80 g). This is stirred for 1 hr and chloroform and water is added. A solid by-product is filtered off. The aqueous phase is extracted with chloroform. The combined chloroform extracts are dried and evaporated to afford 90 g of semisolid. Chromatography on silica gel using 80% acetone in toluene gives 46 g of 3-bromo-2-nitrotoluene: nmr (CDCl3) delta 2.5 (s, 3H) and 7.8 (m, 3H). |
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