Alternatived Products of [ 450412-27-8 ]
Product Details of [ 450412-27-8 ]
| CAS No. : | 450412-27-8 |
MDL No. : | MFCD12025359 |
| Formula : |
C9H8BrIO2
|
Boiling Point : |
- |
| Linear Structure Formula : | - |
InChI Key : | - |
| M.W : | 354.97 g/mol |
Pubchem ID : | - |
| Synonyms : |
|
Safety of [ 450412-27-8 ]
Application In Synthesis of [ 450412-27-8 ]
* 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 [ 450412-27-8 ]
- Downstream synthetic route of [ 450412-27-8 ]
- 1
-
[ 24398-88-7 ]
-
3-bromo-2-iodobenzoic acid ethyl ester
[ No CAS ]
-
[ 450412-27-8 ]
| Yield | Reaction Conditions | Operation in experiment |
| 1: 55%
2: 37% |
Stage #1: ethyl 3-bromobenzoate With tBu2Zn(TMP)Li In tetrahydrofuran at 20℃; for 3h;
Stage #2: With iodine In tetrahydrofuran at 20℃; Further stages.; |
|
|
Stage #1: ethyl 3-bromobenzoate In tetrahydrofuran; hexane; pentane at 20℃; for 3h;
Stage #2: With iodine In tetrahydrofuran; hexane; pentane at 20℃; for 1h; Further stages.; |
|
Reference：
[1]Uchiyama, Masanobu; Miyoshi, Tomoko; Kajihara, Yumiko; Sakamoto, Takao; Otani, Yuko; Ohwada, Tomohiko; Kondo, Yoshinori
[Journal of the American Chemical Society, 2002, vol. 124, # 29, p. 8514 - 8515]
[2]Uchiyama, Masanobu; Kobayashi, Yuri; Furuyama, Taniyuki; Nakamura, Shinji; Kajihara, Yumiko; Miyoshi, Tomoko; Sakamoto, Takao; Kondo, Yoshinori; Morokuma, Keiji
[Journal of the American Chemical Society, 2008, vol. 130, # 2, p. 472 - 480]
- 2
-
[ 24424-99-5 ]
-
[ 138900-55-7 ]
-
[ 450412-27-8 ]
-
[ 1026089-66-6 ]
| Yield | Reaction Conditions | Operation in experiment |
| 37.77% |
Stage #1: 1-(triisopropylsilyl)-1H-pyrrole-3-boronic acid; 4-bromo-1-iodobenzoic acid ethyl ester With caesium carbonate In 1,2-dimethoxyethane; water at 80℃;
Stage #2: di-<i>tert</i>-butyl dicarbonate With tetrabutyl ammonium fluoride In tetrahydrofuran at 20℃; for 2h; |
17.2
Step 2 3-(4-Bromo-2-ethoxycarbonyl-phenyl)-pyrrole-l-carboxylic acid tert-butyl ester; 5-Bromo-2-iodo-benzoic acid ethyl ester (3.93 g, 11.07 mmol), triisopropylsilanyl-lH-pyrrole-3-boronic acid (2.96 g, 11.07 mmol), PdCl2dppf (443 mg, 0.55 mmol) and CsCO3 (4.32 g, 13.28 mmol) were dissolved in 100 ml of a mixture of DME and Water (9:1). The mixture was heated to 8O0C overnight. Upon cooling, the mixture was diluted with water and extracted with Et2O. The ether extracts were washed with brine, dried over Na2SO4 and concentrated under reduced pressure. The residue was immediately diluted in THF. (Boc)2O (2.42 g, 11.07 mmol) was added followed by TBAF (11.07 ml, 11.07 mmol). The mixture was allowed to stir for 2 hours at room temperature, the mixture was diluted with water, extracted with Et2O. The combined ether extracts were washed with brine, dried over Na2SO4, filtered and concentrated under reduced pressure to give 1.648 g (37.77%) of 3-(4-bromo-2-ethoxycarbonyl-phenyl)-pyrrole-l-carboxylic acid tert-butyl ester as a clear oil which used in step 3 without further purification. |
- 3
-
[ 21740-00-1 ]
-
[ 450412-27-8 ]
| Yield | Reaction Conditions | Operation in experiment |
| 100% |
With oxalyl dichloride In dichloromethane at 40℃; for 0.5h; |
17.1
Step 1 5-Bromo-2-iodo-benzoic acid ethyl ester; 5-Bromo-2-iodo-benzoic acid (25.Og, 76.47 mol) was dissolved in CH2Cl2 (75 ml) at room temperature. Oxalyl chloride (14.5 ml, 152.94 mmol) was added and the mixture was stirred at 4O0C for 30 minutes. The mixture was allowed to cool to room temperature and EtOH (6.69 ml, 114.71 mmol) was added. The mixture was concentrated under reduced pressure to give 27.2 g (quantitative) of 5-bromo-2-iodo-benzoic acid ethyl ester as a yellow crystalline solid. |
- 4
-
[ 450412-27-8 ]
-
[ 689291-89-2 ]
- 5
-
[ 450412-27-8 ]
-
[ 1416476-22-6 ]
| Yield | Reaction Conditions | Operation in experiment |
|
Multi-step reaction with 2 steps
1.1: diisobutylaluminium hydride / tetrahydrofuran / 0.75 h / 20 °C / Inert atmosphere; Cooling with ice
1.2: 20 °C
2.1: potassium 2-methylbutan-2-olate / tetrahydrofuran / 0.17 h / Inert atmosphere
2.2: 0.5 h / 20 °C / Cooling with ice; Inert atmosphere |
|
- 6
-
[ 450412-27-8 ]
-
C28H31BrCl2IN2Ru
[ No CAS ]
| Yield | Reaction Conditions | Operation in experiment |
|
Multi-step reaction with 3 steps
1.1: diisobutylaluminium hydride / tetrahydrofuran / 0.75 h / 20 °C / Inert atmosphere; Cooling with ice
1.2: 20 °C
2.1: potassium 2-methylbutan-2-olate / tetrahydrofuran / 0.17 h / Inert atmosphere
2.2: 0.5 h / 20 °C / Cooling with ice; Inert atmosphere
3.1: toluene / 0.5 h / 80 °C |
|
- 7
-
[ 450412-27-8 ]
-
[ 71-43-2 ]
-
[ 493028-83-4 ]
| Yield | Reaction Conditions | Operation in experiment |
| 58% |
With tetrabutylammonium (cyano)trihydroborate for 24h; Irradiation; Photolysis; chemoselective reaction; |
|
- 8
-
[ 450412-27-8 ]
-
(E)-3-(2-(6-(bis(4-(hexyloxy)phenyl)amino)-4,4-di-p-tolyl-4H-indeno[1,2-b]thiophen-2-yl)pyrimidin-5-yl)-2-cyanoacrylic acid
[ No CAS ]
| Yield | Reaction Conditions | Operation in experiment |
|
Multi-step reaction with 8 steps
1.1: n-butyllithium / tetrahydrofuran / 0.33 h / -78 - -40 °C / Inert atmosphere
1.2: 0.5 h / -40 - 20 °C / Inert atmosphere
1.3: 15 h / 20 °C / Inert atmosphere
2.1: tetrahydrofuran / 5 h / Inert atmosphere; Reflux
3.1: acetic acid; hydrogenchloride / dichloromethane / 6 h / 20 °C / Inert atmosphere; Reflux
4.1: palladium diacetate; sodium ethanolate; tributylphosphine / toluene / 14 h / Inert atmosphere; Reflux
5.1: n-butyllithium / tetrahydrofuran / 0.5 h / -78 °C / Inert atmosphere
5.2: 3 h / 20 °C / Inert atmosphere
6.1: trans-bis(triphenylphosphine)palladium dichloride / N,N-dimethyl-formamide / 20 h / 80 °C / Inert atmosphere
7.1: n-butyllithium / tetrahydrofuran / 0.5 h / -100 °C / Inert atmosphere
7.2: -100 °C
8.1: acetic acid; ammonium acetate / 12 h / 90 °C / Inert atmosphere |
|
- 9
-
[ 450412-27-8 ]
-
6-bromo-N,N-bis(4-(hexyloxy)phenyl)-4,4-di-p-tolyl-4H-indeno-[1,2-b]-thiophen-2-amine
[ No CAS ]
| Yield | Reaction Conditions | Operation in experiment |
|
Multi-step reaction with 3 steps
1.1: n-butyllithium / tetrahydrofuran / 0.33 h / -78 - -40 °C / Inert atmosphere
1.2: 0.5 h / -40 - 20 °C / Inert atmosphere
1.3: 15 h / 20 °C / Inert atmosphere
2.1: tetrahydrofuran / 6 h / Inert atmosphere; Reflux
3.1: boron trifluoride diethyl etherate / dichloromethane / 48 h / 20 °C / Inert atmosphere |
|
- 10
-
[ 450412-27-8 ]
-
N,N-bis(4-(hexyloxy)phenyl)-4,4-di-p-tolyl-2-(tributylstannyl)-4H-indeno[1,2-b]thiophen-6-amine
[ No CAS ]
| Yield | Reaction Conditions | Operation in experiment |
|
Multi-step reaction with 5 steps
1.1: n-butyllithium / tetrahydrofuran / 0.33 h / -78 - -40 °C / Inert atmosphere
1.2: 0.5 h / -40 - 20 °C / Inert atmosphere
1.3: 15 h / 20 °C / Inert atmosphere
2.1: tetrahydrofuran / 5 h / Inert atmosphere; Reflux
3.1: acetic acid; hydrogenchloride / dichloromethane / 6 h / 20 °C / Inert atmosphere; Reflux
4.1: palladium diacetate; sodium ethanolate; tributylphosphine / toluene / 14 h / Inert atmosphere; Reflux
5.1: n-butyllithium / tetrahydrofuran / 0.5 h / -78 °C / Inert atmosphere
5.2: 3 h / 20 °C / Inert atmosphere |
|
- 11
-
[ 450412-27-8 ]
-
6-(5-bromopyrimidin-2-yl)-N,N-bis(4-(hexyloxy)phenyl)-4,4-di-p-tolyl-4H-indeno[1,2-b]thiophen-2-amine
[ No CAS ]
| Yield | Reaction Conditions | Operation in experiment |
|
Multi-step reaction with 5 steps
1.1: n-butyllithium / tetrahydrofuran / 0.33 h / -78 - -40 °C / Inert atmosphere
1.2: 0.5 h / -40 - 20 °C / Inert atmosphere
1.3: 15 h / 20 °C / Inert atmosphere
2.1: tetrahydrofuran / 6 h / Inert atmosphere; Reflux
3.1: boron trifluoride diethyl etherate / dichloromethane / 48 h / 20 °C / Inert atmosphere
4.1: tetrahydrofuran / 1 h / -78 °C / Inert atmosphere
4.2: -78 - 20 °C
5.1: trans-bis(triphenylphosphine)palladium dichloride / toluene / 22 h / 1015 °C / Inert atmosphere |
|
- 12
-
[ 450412-27-8 ]
-
N,N-bis(4-(hexyloxy)phenyl)-4,4-di-p-tolyl-6-(tributylstannyl)-4H-indeno[1,2-b]-thiophen-2-amine
[ No CAS ]
| Yield | Reaction Conditions | Operation in experiment |
|
Multi-step reaction with 4 steps
1.1: n-butyllithium / tetrahydrofuran / 0.33 h / -78 - -40 °C / Inert atmosphere
1.2: 0.5 h / -40 - 20 °C / Inert atmosphere
1.3: 15 h / 20 °C / Inert atmosphere
2.1: tetrahydrofuran / 6 h / Inert atmosphere; Reflux
3.1: boron trifluoride diethyl etherate / dichloromethane / 48 h / 20 °C / Inert atmosphere
4.1: tetrahydrofuran / 1 h / -78 °C / Inert atmosphere
4.2: -78 - 20 °C |
|
- 13
-
[ 450412-27-8 ]
-
2-(2-(bis(4-(hexyloxy)phenyl)amino)-4,4-di-p-tolyl-4H-indeno[1,2-b]thiophen-6-yl)pyrimidine-5-carbaldehyde
[ No CAS ]
| Yield | Reaction Conditions | Operation in experiment |
|
Multi-step reaction with 6 steps
1.1: n-butyllithium / tetrahydrofuran / 0.33 h / -78 - -40 °C / Inert atmosphere
1.2: 0.5 h / -40 - 20 °C / Inert atmosphere
1.3: 15 h / 20 °C / Inert atmosphere
2.1: tetrahydrofuran / 6 h / Inert atmosphere; Reflux
3.1: boron trifluoride diethyl etherate / dichloromethane / 48 h / 20 °C / Inert atmosphere
4.1: tetrahydrofuran / 1 h / -78 °C / Inert atmosphere
4.2: -78 - 20 °C
5.1: trans-bis(triphenylphosphine)palladium dichloride / toluene / 22 h / 1015 °C / Inert atmosphere
6.1: n-butyllithium / tetrahydrofuran / 0.5 h / -100 °C / Inert atmosphere
6.2: -100 °C |
|
- 14
-
[ 450412-27-8 ]
-
(E)-3-(2-(2-(bis(4-(hexyloxy)phenyl)amino)-4,4-di-p-tolyl-4H-indeno[1,2-b]-thiophen-6-yl)pyrimidin-5-yl)-2-cyanoacrylic acid
[ No CAS ]
| Yield | Reaction Conditions | Operation in experiment |
|
Multi-step reaction with 7 steps
1.1: n-butyllithium / tetrahydrofuran / 0.33 h / -78 - -40 °C / Inert atmosphere
1.2: 0.5 h / -40 - 20 °C / Inert atmosphere
1.3: 15 h / 20 °C / Inert atmosphere
2.1: tetrahydrofuran / 6 h / Inert atmosphere; Reflux
3.1: boron trifluoride diethyl etherate / dichloromethane / 48 h / 20 °C / Inert atmosphere
4.1: tetrahydrofuran / 1 h / -78 °C / Inert atmosphere
4.2: -78 - 20 °C
5.1: trans-bis(triphenylphosphine)palladium dichloride / toluene / 22 h / 1015 °C / Inert atmosphere
6.1: n-butyllithium / tetrahydrofuran / 0.5 h / -100 °C / Inert atmosphere
6.2: -100 °C
7.1: acetic acid; ammonium acetate / 12 h / 90 °C / Inert atmosphere |
|
- 15
-
[ 450412-27-8 ]
-
C25H21BrOS
[ No CAS ]
| Yield | Reaction Conditions | Operation in experiment |
|
Multi-step reaction with 2 steps
1.1: n-butyllithium / tetrahydrofuran / 0.33 h / -78 - -40 °C / Inert atmosphere
1.2: 0.5 h / -40 - 20 °C / Inert atmosphere
1.3: 15 h / 20 °C / Inert atmosphere
2.1: tetrahydrofuran / 5 h / Inert atmosphere; Reflux |
|
- 16
-
[ 450412-27-8 ]
-
C49H54BrNO3S
[ No CAS ]
| Yield | Reaction Conditions | Operation in experiment |
|
Multi-step reaction with 2 steps
1.1: n-butyllithium / tetrahydrofuran / 0.33 h / -78 - -40 °C / Inert atmosphere
1.2: 0.5 h / -40 - 20 °C / Inert atmosphere
1.3: 15 h / 20 °C / Inert atmosphere
2.1: tetrahydrofuran / 6 h / Inert atmosphere; Reflux |
|
- 17
-
[ 450412-27-8 ]
-
6-bromo-4,4-di-p-tolyl-4H-indeno[1,2-b]thiophene
[ No CAS ]
| Yield | Reaction Conditions | Operation in experiment |
|
Multi-step reaction with 3 steps
1.1: n-butyllithium / tetrahydrofuran / 0.33 h / -78 - -40 °C / Inert atmosphere
1.2: 0.5 h / -40 - 20 °C / Inert atmosphere
1.3: 15 h / 20 °C / Inert atmosphere
2.1: tetrahydrofuran / 5 h / Inert atmosphere; Reflux
3.1: acetic acid; hydrogenchloride / dichloromethane / 6 h / 20 °C / Inert atmosphere; Reflux |
|
- 18
-
[ 450412-27-8 ]
-
N,N-bis(4-(hexyloxy)phenyl)-4,4-di-p-tolyl-4H-indeno[1,2-b]thiophen-6-amine
[ No CAS ]
| Yield | Reaction Conditions | Operation in experiment |
|
Multi-step reaction with 4 steps
1.1: n-butyllithium / tetrahydrofuran / 0.33 h / -78 - -40 °C / Inert atmosphere
1.2: 0.5 h / -40 - 20 °C / Inert atmosphere
1.3: 15 h / 20 °C / Inert atmosphere
2.1: tetrahydrofuran / 5 h / Inert atmosphere; Reflux
3.1: acetic acid; hydrogenchloride / dichloromethane / 6 h / 20 °C / Inert atmosphere; Reflux
4.1: palladium diacetate; sodium ethanolate; tributylphosphine / toluene / 14 h / Inert atmosphere; Reflux |
|
- 19
-
[ 450412-27-8 ]
-
2-(5-bromopyrimidin-2-yl)-N,N-bis(4-(hexyloxy)phenyl)-4,4-di-p-tolyl-4H-indeno[1,2-b]thiophen-6-amine
[ No CAS ]
| Yield | Reaction Conditions | Operation in experiment |
|
Multi-step reaction with 6 steps
1.1: n-butyllithium / tetrahydrofuran / 0.33 h / -78 - -40 °C / Inert atmosphere
1.2: 0.5 h / -40 - 20 °C / Inert atmosphere
1.3: 15 h / 20 °C / Inert atmosphere
2.1: tetrahydrofuran / 5 h / Inert atmosphere; Reflux
3.1: acetic acid; hydrogenchloride / dichloromethane / 6 h / 20 °C / Inert atmosphere; Reflux
4.1: palladium diacetate; sodium ethanolate; tributylphosphine / toluene / 14 h / Inert atmosphere; Reflux
5.1: n-butyllithium / tetrahydrofuran / 0.5 h / -78 °C / Inert atmosphere
5.2: 3 h / 20 °C / Inert atmosphere
6.1: trans-bis(triphenylphosphine)palladium dichloride / N,N-dimethyl-formamide / 20 h / 80 °C / Inert atmosphere |
|
- 20
-
[ 450412-27-8 ]
-
2-(6-(bis(4-(hexyloxy)phenyl)amino)-4,4-di-p-tolyl-4H-indeno[1,2-b]thiophen-2-yl)pyrimidine-5-carbaldehyde
[ No CAS ]
| Yield | Reaction Conditions | Operation in experiment |
|
Multi-step reaction with 7 steps
1.1: n-butyllithium / tetrahydrofuran / 0.33 h / -78 - -40 °C / Inert atmosphere
1.2: 0.5 h / -40 - 20 °C / Inert atmosphere
1.3: 15 h / 20 °C / Inert atmosphere
2.1: tetrahydrofuran / 5 h / Inert atmosphere; Reflux
3.1: acetic acid; hydrogenchloride / dichloromethane / 6 h / 20 °C / Inert atmosphere; Reflux
4.1: palladium diacetate; sodium ethanolate; tributylphosphine / toluene / 14 h / Inert atmosphere; Reflux
5.1: n-butyllithium / tetrahydrofuran / 0.5 h / -78 °C / Inert atmosphere
5.2: 3 h / 20 °C / Inert atmosphere
6.1: trans-bis(triphenylphosphine)palladium dichloride / N,N-dimethyl-formamide / 20 h / 80 °C / Inert atmosphere
7.1: n-butyllithium / tetrahydrofuran / 0.5 h / -100 °C / Inert atmosphere
7.2: -100 °C |
|
- 21
-
[ 1306754-00-6 ]
-
[ 450412-27-8 ]
-
ethyl 2-(5-(bis(4-(hexyloxy)phenyl)amino)thiophen-2-yl)-5-bromo-benzoate
[ No CAS ]
| Yield | Reaction Conditions | Operation in experiment |
| 85.9% |
Stage #1: 2-[N,N-bis-(4-hexyloxyphenyl)amino]thiophene With n-butyllithium In tetrahydrofuran at -78 - -40℃; for 0.333333h; Inert atmosphere;
Stage #2: With zinc(II) chloride In tetrahydrofuran at -40 - 20℃; for 0.5h; Inert atmosphere;
Stage #3: 4-bromo-1-iodobenzoic acid ethyl ester With tetrakis(triphenylphosphine) palladium(0) In tetrahydrofuran at 20℃; for 15h; Inert atmosphere; |
|
- 22
-
[ 188290-36-0 ]
-
[ 450412-27-8 ]
-
ethyl 5-bromo-2-(thiophen-2-yl)benzoate
[ No CAS ]
| Yield | Reaction Conditions | Operation in experiment |
| 89.7% |
Stage #1: thiophene With n-butyllithium In tetrahydrofuran at -78 - -40℃; for 0.333333h; Inert atmosphere;
Stage #2: With zinc(II) chloride In tetrahydrofuran at -40 - 20℃; for 0.5h; Inert atmosphere;
Stage #3: 4-bromo-1-iodobenzoic acid ethyl ester With tetrakis(triphenylphosphine) palladium(0) In tetrahydrofuran at 20℃; for 15h; Inert atmosphere; |
|
- 23
-
[ 450412-27-8 ]
-
C16H16BrIO2
[ No CAS ]
| Yield | Reaction Conditions | Operation in experiment |
|
Multi-step reaction with 2 steps
1: sodium hydride / tetrahydrofuran / 26 h / 20 °C / Reflux
2: potassium carbonate / acetone / Reflux |
|
Reference：
[1]Yuan, Zhenbo; Feng, Ziwen; Zeng, Yuye; Zhao, Xiaobin; Lin, Aijun; Yao, Hequan
[Angewandte Chemie - International Edition, 2019, vol. 58, # 9, p. 2884 - 2888][Angew. Chem., 2019, vol. 131, # 9, p. 2910 - 2914,5]
- 24
-
[ 450412-27-8 ]
-
1-(1-(5-bromo-2-iodobenzoyl)cyclopent-3-en-1-yl)ethan-1-one
[ No CAS ]
| Yield | Reaction Conditions | Operation in experiment |
|
Multi-step reaction with 3 steps
1: sodium hydride / tetrahydrofuran / 26 h / 20 °C / Reflux
2: potassium carbonate / acetone / Reflux
3: tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride / dichloromethane / 2 h / 40 °C |
|
Reference：
[1]Yuan, Zhenbo; Feng, Ziwen; Zeng, Yuye; Zhao, Xiaobin; Lin, Aijun; Yao, Hequan
[Angewandte Chemie - International Edition, 2019, vol. 58, # 9, p. 2884 - 2888][Angew. Chem., 2019, vol. 131, # 9, p. 2910 - 2914,5]
- 25
-
[ 450412-27-8 ]
-
(5-bromo-2-iodophenyl)(cyclopent-3-en-1-yl)methanone
[ No CAS ]
| Yield | Reaction Conditions | Operation in experiment |
|
Multi-step reaction with 4 steps
1: sodium hydride / tetrahydrofuran / 26 h / 20 °C / Reflux
2: potassium carbonate / acetone / Reflux
3: tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride / dichloromethane / 2 h / 40 °C
4: lithium hydroxide monohydrate / ethanol; water / 4 h / 20 °C |
|
Reference：
[1]Yuan, Zhenbo; Feng, Ziwen; Zeng, Yuye; Zhao, Xiaobin; Lin, Aijun; Yao, Hequan
[Angewandte Chemie - International Edition, 2019, vol. 58, # 9, p. 2884 - 2888][Angew. Chem., 2019, vol. 131, # 9, p. 2910 - 2914,5]
- 26
-
[ 141-78-6 ]
-
[ 450412-27-8 ]
-
C11H10BrIO3
[ No CAS ]
| Yield | Reaction Conditions | Operation in experiment |
|
With sodium hydride In tetrahydrofuran at 20℃; for 26h; Reflux; |
|
Reference：
[1]Yuan, Zhenbo; Feng, Ziwen; Zeng, Yuye; Zhao, Xiaobin; Lin, Aijun; Yao, Hequan
[Angewandte Chemie - International Edition, 2019, vol. 58, # 9, p. 2884 - 2888][Angew. Chem., 2019, vol. 131, # 9, p. 2910 - 2914,5]
- 27
-
[ 67-64-1 ]
-
[ 450412-27-8 ]
-
C10H8BrIO2
[ No CAS ]
| Yield | Reaction Conditions | Operation in experiment |
|
With sodium hydride In tetrahydrofuran at 20℃; for 26h; Reflux; |
|
Reference：
[1]Yuan, Zhenbo; Feng, Ziwen; Zeng, Yuye; Zhao, Xiaobin; Lin, Aijun; Yao, Hequan
[Angewandte Chemie - International Edition, 2019, vol. 58, # 9, p. 2884 - 2888][Angew. Chem., 2019, vol. 131, # 9, p. 2910 - 2914,5]
- 28
-
[ 64-17-5 ]
-
[ 21740-00-1 ]
-
[ 450412-27-8 ]
| Yield | Reaction Conditions | Operation in experiment |
| 92% |
With acetyl chloride In ethanol Reflux; |
|
- 29
-
[ 30568-40-2 ]
-
[ 450412-27-8 ]
-
3-bromo-7,7,9-trimethyl-6,7-dihydro-5H-dibenzo[c,e]azepin-5-one
[ No CAS ]
| Yield | Reaction Conditions | Operation in experiment |
| 87% |
With silver(I) acetate; palladium diacetate In acetic acid at 100℃; for 14h; Sealed tube; |
|
- 30
-
[ 1765-93-1 ]
-
[ 450412-27-8 ]
-
C15H12BrFO2
[ No CAS ]
| Yield | Reaction Conditions | Operation in experiment |
|
With bis-triphenylphosphine-palladium(II) chloride; potassium carbonate In water; N,N-dimethyl-formamide at 60℃; for 6h; Inert atmosphere; |
|
- 31
-
[ 1679-18-1 ]
-
[ 450412-27-8 ]
-
C15H12BrClO2
[ No CAS ]
| Yield | Reaction Conditions | Operation in experiment |
|
With bis-triphenylphosphine-palladium(II) chloride; potassium carbonate In water; N,N-dimethyl-formamide at 60℃; for 6h; Inert atmosphere; |
|
- 32
-
[ 450412-27-8 ]
-
[ 69200-18-6 ]
| Yield | Reaction Conditions | Operation in experiment |
|
Multi-step reaction with 2 steps
1: bis-triphenylphosphine-palladium(II) chloride; potassium carbonate / N,N-dimethyl-formamide; water / 6 h / 60 °C / Inert atmosphere
2: potassium hydroxide / water; ethanol / 8 h / 80 °C |
|
- 33
-
[ 450412-27-8 ]
-
5-bromo-2-(4'-methylphenyl)benzoic acid
[ No CAS ]
| Yield | Reaction Conditions | Operation in experiment |
|
Multi-step reaction with 2 steps
1: bis-triphenylphosphine-palladium(II) chloride; potassium carbonate / N,N-dimethyl-formamide; water / 6 h / 60 °C / Inert atmosphere
2: potassium hydroxide / water; ethanol / 8 h / 80 °C |
|
- 34
-
[ 450412-27-8 ]
-
5-bromo-2-(4'-tert-butylphenyl)benzoic acid
[ No CAS ]
| Yield | Reaction Conditions | Operation in experiment |
|
Multi-step reaction with 2 steps
1: bis-triphenylphosphine-palladium(II) chloride; potassium carbonate / N,N-dimethyl-formamide; water / 6 h / 60 °C / Inert atmosphere
2: potassium hydroxide / water; ethanol / 8 h / 80 °C |
|
- 35
-
[ 450412-27-8 ]
-
5-bromo-2-(4'-methoxyphenyl)benzoic acid
[ No CAS ]
| Yield | Reaction Conditions | Operation in experiment |
|
Multi-step reaction with 2 steps
1: bis-triphenylphosphine-palladium(II) chloride; potassium carbonate / N,N-dimethyl-formamide; water / 6 h / 60 °C / Inert atmosphere
2: potassium hydroxide / water; ethanol / 8 h / 80 °C |
|
- 36
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[ 450412-27-8 ]
-
5-bromo-2-(4'-fluorophenyl)benzoic acid
[ No CAS ]
| Yield | Reaction Conditions | Operation in experiment |
|
Multi-step reaction with 2 steps
1: bis-triphenylphosphine-palladium(II) chloride; potassium carbonate / N,N-dimethyl-formamide; water / 6 h / 60 °C / Inert atmosphere
2: potassium hydroxide / water; ethanol / 8 h / 80 °C |
|
- 37
-
[ 450412-27-8 ]
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5-bromo-2-(4'-chlorophenyl)benzoic acid
[ No CAS ]
| Yield | Reaction Conditions | Operation in experiment |
|
Multi-step reaction with 2 steps
1: bis-triphenylphosphine-palladium(II) chloride; potassium carbonate / N,N-dimethyl-formamide; water / 6 h / 60 °C / Inert atmosphere
2: potassium hydroxide / water; ethanol / 8 h / 80 °C |
|
- 38
-
[ 450412-27-8 ]
-
[ 1447543-95-4 ]
| Yield | Reaction Conditions | Operation in experiment |
|
Multi-step reaction with 3 steps
1: bis-triphenylphosphine-palladium(II) chloride; potassium carbonate / N,N-dimethyl-formamide; water / 6 h / 60 °C / Inert atmosphere
2: potassium hydroxide / water; ethanol / 8 h / 80 °C
3: N-iodo-succinimide / 1,2-dichloro-ethane / 5 h / 38 - 40 °C / Inert atmosphere; Irradiation |
|
- 39
-
[ 450412-27-8 ]
-
3,4-(2'-bromo)benzo-7-methylcoumarin
[ No CAS ]
| Yield | Reaction Conditions | Operation in experiment |
|
Multi-step reaction with 3 steps
1: bis-triphenylphosphine-palladium(II) chloride; potassium carbonate / N,N-dimethyl-formamide; water / 6 h / 60 °C / Inert atmosphere
2: potassium hydroxide / water; ethanol / 8 h / 80 °C
3: N-chloro-succinimide; sodium iodide / 1,2-dichloro-ethane / 7 h / 70 °C / Inert atmosphere; Irradiation |
|
- 40
-
[ 450412-27-8 ]
-
3,4-(2'-bromo)benzo-7-(tert-butyl)coumarin
[ No CAS ]
| Yield | Reaction Conditions | Operation in experiment |
|
Multi-step reaction with 3 steps
1: bis-triphenylphosphine-palladium(II) chloride; potassium carbonate / N,N-dimethyl-formamide; water / 6 h / 60 °C / Inert atmosphere
2: potassium hydroxide / water; ethanol / 8 h / 80 °C
3: N-chloro-succinimide; sodium iodide / 1,2-dichloro-ethane / 7 h / 70 °C / Inert atmosphere; Irradiation |
|
- 41
-
[ 450412-27-8 ]
-
3,4-(2'-bromo)benzo-7-methoxycoumarin
[ No CAS ]
| Yield | Reaction Conditions | Operation in experiment |
|
Multi-step reaction with 3 steps
1: bis-triphenylphosphine-palladium(II) chloride; potassium carbonate / N,N-dimethyl-formamide; water / 6 h / 60 °C / Inert atmosphere
2: potassium hydroxide / water; ethanol / 8 h / 80 °C
3: N-chloro-succinimide; sodium iodide / 1,2-dichloro-ethane / 21 h / 70 °C / Inert atmosphere; Irradiation |
|
- 42
-
[ 450412-27-8 ]
-
3,4-(2'-bromo)benzo-7-fluorocoumarin
[ No CAS ]
| Yield | Reaction Conditions | Operation in experiment |
|
Multi-step reaction with 3 steps
1: bis-triphenylphosphine-palladium(II) chloride; potassium carbonate / N,N-dimethyl-formamide; water / 6 h / 60 °C / Inert atmosphere
2: potassium hydroxide / water; ethanol / 8 h / 80 °C
3: N-iodo-succinimide / 1,2-dichloro-ethane / 7 h / 38 - 40 °C / Inert atmosphere; Irradiation |
|
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