Alternatived Products of [ 18706-22-4 ]
Product Details of [ 18706-22-4 ]
| CAS No. : | 18706-22-4 |
MDL No. : | MFCD00276589 |
| Formula : |
C10H5ClF3NO
|
Boiling Point : |
- |
| Linear Structure Formula : | - |
InChI Key : | - |
| M.W : |
247.60
|
Pubchem ID : | - |
| Synonyms : |
|
Safety of [ 18706-22-4 ]
| Signal Word: | |
Class: | |
| Precautionary Statements: | |
UN#: | |
| Hazard Statements: | |
Packing Group: | |
Application In Synthesis of [ 18706-22-4 ]
* 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.
- Downstream synthetic route of [ 18706-22-4 ]
- 1
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[ 95-51-2 ]
-
[ 372-31-6 ]
-
[ 18706-22-4 ]
| Yield | Reaction Conditions | Operation in experiment |
| 65% |
Stage #1: ethyl 4,4,4-trifluoroacetoacetate With polyphosphoric acid at 100℃; for 0.25h;
Stage #2: o-chloroaniline at 100 - 150℃; for 3h; |
31.1 Step 1
To a well-stirred solution of polyphosphoric acid (70 g) at 100°C was added ethyl 4,4,4-trifluoroacetoacetate (19.6 ml, 133 mmol) dropwise, and the mixture was stirred for 15 min. 2-Chloroaniline (14 ml, 133 mmol) was then added at 100°C dropwise, and the reaction was warmed to 150°C and stirred for 3h. The slurry was slowly poured at RT over ice-cold water then stirred overnight at RT. The mixture was filtered, and the solid was taken up in DCM/MeOH 1 : 1, concentrated to ~20 ml, then poured into hexanes (700 ml). The resulting solid was filtered, rinsing with hexanes, and dried in vacuo to give the product of Step 1 (21.35 g, 65% yield). |
- 2
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[ 18706-22-4 ]
-
C10H6BrClF3N
[ No CAS ]
| Yield | Reaction Conditions | Operation in experiment |
| 100% |
With phosphorus(V) oxybromide In acetonitrile for 1.5h; Reflux; |
31.2 Step 2
To a solution of the product of Step 1 (10 g, 40.4 mmol) in MeCN (250 ml) at RT was added phosphorus oxybromide (13.32 g, 46.4 mmol), and the mixture was warmed to reflux and stirred for 90 min. The mixture was poured at RT into sat. aq. aHC03 and extracted with EtOAc. The combined organic fractions were washed with brine, dried over Na2S04, filtered and concentrated in vacuo. The residue was purified by column chromatography over silica gel (eluting with Hexanes/EtOAc 99: 1 to 50:50) to provide the product of Step 2 (12.5 g, 100% yield) as a white solid. |
- 3
-
[ 18706-22-4 ]
-
C10H7BBrClF3NO2
[ No CAS ]
| Yield | Reaction Conditions | Operation in experiment |
|
Multi-step reaction with 2 steps
1.1: phosphorus(V) oxybromide / acetonitrile / 1.5 h / Reflux
2.1: diisopropylamine; n-butyllithium / tetrahydrofuran; hexane / 1.5 h / -78 °C
2.2: 3 h / -78 °C |
|
- 4
-
[ 18706-22-4 ]
-
C10H6BrClF3NO
[ No CAS ]
| Yield | Reaction Conditions | Operation in experiment |
|
Multi-step reaction with 3 steps
1.1: phosphorus(V) oxybromide / acetonitrile / 1.5 h / Reflux
2.1: diisopropylamine; n-butyllithium / tetrahydrofuran; hexane / 1.5 h / -78 °C
2.2: 3 h / -78 °C
3.1: 3-chloro-benzenecarboperoxoic acid / dichloromethane |
|
- 5
-
[ 18706-22-4 ]
-
C12H9ClF3NO2
[ No CAS ]
| Yield | Reaction Conditions | Operation in experiment |
|
Multi-step reaction with 4 steps
1.1: phosphorus(V) oxybromide / acetonitrile / 1.5 h / Reflux
2.1: diisopropylamine; n-butyllithium / tetrahydrofuran; hexane / 1.5 h / -78 °C
2.2: 3 h / -78 °C
3.1: 3-chloro-benzenecarboperoxoic acid / dichloromethane
4.1: tetrakis(triphenylphosphine) palladium(0) / 1,4-dioxane / 110 °C |
|
- 6
-
[ 18706-22-4 ]
-
[ 1565779-75-0 ]
| Yield | Reaction Conditions | Operation in experiment |
|
Multi-step reaction with 5 steps
1.1: phosphorus(V) oxybromide / acetonitrile / 1.5 h / Reflux
2.1: diisopropylamine; n-butyllithium / tetrahydrofuran; hexane / 1.5 h / -78 °C
2.2: 3 h / -78 °C
3.1: 3-chloro-benzenecarboperoxoic acid / dichloromethane
4.1: tetrakis(triphenylphosphine) palladium(0) / 1,4-dioxane / 110 °C
5.1: benzoic acid; pyrrolidine / methanol / 72 h / 60 °C / Molecular sieve |
|
- 7
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[ 18706-22-4 ]
-
[ 1565779-76-1 ]
| Yield | Reaction Conditions | Operation in experiment |
|
Multi-step reaction with 6 steps
1.1: phosphorus(V) oxybromide / acetonitrile / 1.5 h / Reflux
2.1: diisopropylamine; n-butyllithium / tetrahydrofuran; hexane / 1.5 h / -78 °C
2.2: 3 h / -78 °C
3.1: 3-chloro-benzenecarboperoxoic acid / dichloromethane
4.1: tetrakis(triphenylphosphine) palladium(0) / 1,4-dioxane / 110 °C
5.1: benzoic acid; pyrrolidine / methanol / 72 h / 60 °C / Molecular sieve
6.1: sodium tetrahydroborate / tetrahydrofuran; methanol / 1 h / 0 °C |
|
- 8
-
[ 18706-22-4 ]
-
[ 1565779-77-2 ]
| Yield | Reaction Conditions | Operation in experiment |
|
Multi-step reaction with 7 steps
1.1: phosphorus(V) oxybromide / acetonitrile / 1.5 h / Reflux
2.1: diisopropylamine; n-butyllithium / tetrahydrofuran; hexane / 1.5 h / -78 °C
2.2: 3 h / -78 °C
3.1: 3-chloro-benzenecarboperoxoic acid / dichloromethane
4.1: tetrakis(triphenylphosphine) palladium(0) / 1,4-dioxane / 110 °C
5.1: benzoic acid; pyrrolidine / methanol / 72 h / 60 °C / Molecular sieve
6.1: sodium tetrahydroborate / tetrahydrofuran; methanol / 1 h / 0 °C
7.1: methanesulfonyl chloride; N-ethyl-N,N-diisopropylamine / dichloromethane / 0 - 20 °C |
|
- 9
-
[ 18706-22-4 ]
-
[ 1565779-78-3 ]
| Yield | Reaction Conditions | Operation in experiment |
|
Multi-step reaction with 8 steps
1.1: phosphorus(V) oxybromide / acetonitrile / 1.5 h / Reflux
2.1: diisopropylamine; n-butyllithium / tetrahydrofuran; hexane / 1.5 h / -78 °C
2.2: 3 h / -78 °C
3.1: 3-chloro-benzenecarboperoxoic acid / dichloromethane
4.1: tetrakis(triphenylphosphine) palladium(0) / 1,4-dioxane / 110 °C
5.1: benzoic acid; pyrrolidine / methanol / 72 h / 60 °C / Molecular sieve
6.1: sodium tetrahydroborate / tetrahydrofuran; methanol / 1 h / 0 °C
7.1: methanesulfonyl chloride; N-ethyl-N,N-diisopropylamine / dichloromethane / 0 - 20 °C
8.1: nickel(II) chloride hexahydrate; lithium borohydride / tetrahydrofuran; methanol / 1.25 h / -78 - 0 °C |
|
- 10
-
[ 18706-22-4 ]
-
[ 1565782-09-3 ]
| Yield | Reaction Conditions | Operation in experiment |
|
Multi-step reaction with 9 steps
1.1: phosphorus(V) oxybromide / acetonitrile / 1.5 h / Reflux
2.1: diisopropylamine; n-butyllithium / tetrahydrofuran; hexane / 1.5 h / -78 °C
2.2: 3 h / -78 °C
3.1: 3-chloro-benzenecarboperoxoic acid / dichloromethane
4.1: tetrakis(triphenylphosphine) palladium(0) / 1,4-dioxane / 110 °C
5.1: benzoic acid; pyrrolidine / methanol / 72 h / 60 °C / Molecular sieve
6.1: sodium tetrahydroborate / tetrahydrofuran; methanol / 1 h / 0 °C
7.1: methanesulfonyl chloride; N-ethyl-N,N-diisopropylamine / dichloromethane / 0 - 20 °C
8.1: nickel(II) chloride hexahydrate; lithium borohydride / tetrahydrofuran; methanol / 1.25 h / -78 - 0 °C
9.1: lithium hydroxide monohydrate / water; tetrahydrofuran; methanol / 40 °C |
|
- 11
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[ 18706-22-4 ]
-
[ 1565771-41-6 ]
| Yield | Reaction Conditions | Operation in experiment |
|
Multi-step reaction with 10 steps
1.1: phosphorus(V) oxybromide / acetonitrile / 1.5 h / Reflux
2.1: diisopropylamine; n-butyllithium / tetrahydrofuran; hexane / 1.5 h / -78 °C
2.2: 3 h / -78 °C
3.1: 3-chloro-benzenecarboperoxoic acid / dichloromethane
4.1: tetrakis(triphenylphosphine) palladium(0) / 1,4-dioxane / 110 °C
5.1: benzoic acid; pyrrolidine / methanol / 72 h / 60 °C / Molecular sieve
6.1: sodium tetrahydroborate / tetrahydrofuran; methanol / 1 h / 0 °C
7.1: methanesulfonyl chloride; N-ethyl-N,N-diisopropylamine / dichloromethane / 0 - 20 °C
8.1: nickel(II) chloride hexahydrate; lithium borohydride / tetrahydrofuran; methanol / 1.25 h / -78 - 0 °C
9.1: lithium hydroxide monohydrate / water; tetrahydrofuran; methanol / 40 °C
10.1: 1,1'-carbonyldiimidazole / tetrahydrofuran / 5 h / 70 °C
10.2: 8 h / 50 °C |
|
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