Alternatived Products of [ 112279-62-6 ]
Product Details of [ 112279-62-6 ]
| CAS No. : | 112279-62-6 |
MDL No. : | MFCD16658642 |
| Formula : |
C7H3BrF2N2
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Boiling Point : |
- |
| Linear Structure Formula : | - |
InChI Key : | - |
| M.W : |
233.01
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Pubchem ID : | - |
| Synonyms : |
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Safety of [ 112279-62-6 ]
| Signal Word: | |
Class: | |
| Precautionary Statements: | |
UN#: | |
| Hazard Statements: | |
Packing Group: | |
Application In Synthesis of [ 112279-62-6 ]
* 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.
- Upstream synthesis route of [ 112279-62-6 ]
- Downstream synthetic route of [ 112279-62-6 ]
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[ 75-09-2 ]
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[ 7732-18-5 ]
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[ 112279-61-5 ]
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[ 112279-62-6 ]
| Yield | Reaction Conditions | Operation in experiment |
| 71% |
With bromine In acetic acid |
16 Preparation of 4-amino-3-bromo-2,5-difluorobenzonitrile
EXAMPLE 16 Preparation of 4-amino-3-bromo-2,5-difluorobenzonitrile A mixture of 1.65 mL of Br2, 2 mL of H2 O and 5 g of 4-amino-2,5-difluorobenzonitrile in 50 mL of AcOH is stirred at 20°-25° for 16 hours. The solvents are removed in vacuo and the residue partitioned between 100 mL of H2 O and 3*200 ml of CH2 Cl2. The CH2 Cl2 extracts are washed with H2 O, saturated NaHCO3, H2 O (100 mL each), dried with Na2 SO4 and evaporated in vacuo to give 6.89 g of crude 4-amino-3-bromo-2,5-difluorobenzonitrile. This is purified by dry-column chromatography using SiO2 to give 5.38 g (71% yield). Recrystallization from CH2 Cl2 /hexane affords analytically pure material, m.p. 106°-108° C. Anal. Calcd. for C7 H3 BrF2 N2: C, 36.08, H, 1.3; N, 12.02. Found: C, 36.08; H, 1.23; N, 12.04. |
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[ 112279-61-5 ]
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[ 112279-62-6 ]
| Yield | Reaction Conditions | Operation in experiment |
| 71% |
With bromine In dichloromethane; water; acetic acid |
16 Preparation of 4-amino-3-bromo-2,5-difluorobenzonitrile
Example 16 Preparation of 4-amino-3-bromo-2,5-difluorobenzonitrile A mixture of 1.65 mL of Br2, 2 mL of H2O and 5g of 4-amino-2,5-difluorobenzonitrile in 50 mL of AcOH is stirred at 20°-25° for 16 hours. The solvents are removed in vacuo and the residue partitioned between 100 mL of H2O and 3 x 200 ml of CH2Cl2. The CH2Cl2 extracts are washed with H2O, saturated NaHCO3, H2O (100 mL each), dried with Na2SO4 and evaporated in vacuo to give 6.89g of crude 4-amino-3-bromo-2,5-difluorobenzonitrile. This is purified by dry-column chromatography using SiO2 to give 5.38g (71% yield). Recrystallization from CH2-Cl2/hexane affords analytically pure material, m.p. 106°-108°C. |
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With bromine In water; acetic acid at 20℃; |
19.2
5.0 g of 4-amino-2,5-difluorobenzonitrile, 5.13 g bromine, 2 ml_ water, and 50 ml_ glacial acetic acid were placed under nitrogen in an oven-dried flask and stirred overnight at room temperature. The reaction was concentrated, diluted with methylene chloride, extracted with water and 5% sodium carbonate, dried over sodium sulfate, filtered, concentrated, and purified by flash chromatography on silica. The product fractions were concentrated and vacuum dried to give 6.9 g of product. GCMS (M) 232; 1 H NMR (400 MHz, DMSO-c/6) δ ppm 6.89 (s, 2 H) 7.71 (dd, J= 11.14, 6.04 Hz, 1 H). |
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With bromine; acetic acid In water at 20℃; for 4h; |
Step B: 4-amino-3 -bromo-2,5 -difluorobenzonitrile
To a solution of 4-amino-2,5- difluorobanzonitrile (19 g, 0.13 mol) in 190 mL of AcOH and 8 mL of H20 was added Br2 (6.27 mL, 0.13 mol) dropwise. The resulting mixture was stirred at room temperature for 4 hours. The mixture was then poured into water, and the white precipitates were filtered, washed with water and dried to give 4-amino-3-bromo-2,5-difluorobenzonitrile. |
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[ 112279-62-6 ]
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[ 112279-64-8 ]
| Yield | Reaction Conditions | Operation in experiment |
|
With water; hypophosphorous acid; acetic acid; sodium nitrite; at 0 - 20℃; for 1.0h; |
4.6 g of 4-amino-3-bromo-2,5-difluorobenzaldehyde, 110 ml_ glacial acetic acid, and 54 ml_ of hypophosphorous acid were placed under nitrogen in an oven-dried flask and chilled to 00C. 1.96 g of sodium nitrite dissolved with 11 ml_ water was added to the reaction mixture from an addition funnel maintaining reaction temperature below 15C. The mixture was warmed to room temperature and stirred for 1 hour, diluted into 300 ml_ of ice water and extracted 3 times with methylene chloride. The combined organic layers were extracted with water, 2 times with 10% sodium hydroxide, 2 times with water, <n="94"/>dried over sodium sulfate, filtered, concentrated, and purified by flash chromatography on silica. The product fractions were concentrated and dried under vacuum to give 2.79 g of product. GCMS (M)222; 1 H NMR (400 MHz, DMSO-c/6) delta ppm 7.66 (ddd, J=8.06, 4.83, 3.22 Hz, 1 H) 8.12 (ddd, J=7.52, 5.37, 3.22 Hz, 1 H) 10.13 (d, J=2.42 Hz, 1 H). |
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[ 112279-62-6 ]
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[ 1159186-56-7 ]
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