[ CAS No. 450412-27-8 ]

Name: 450412-27-8|Ethyl 5-bromo-2-iodobenzoate|95+%
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Product Details of [ 450412-27-8 ]

CAS No. :	450412-27-8	MDL No. :	MFCD12025359
Formula :	C₉H₈BrIO₂	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	JWUQSSZXGVRFDZ-UHFFFAOYSA-N
M.W :	354.97 g/mol	Pubchem ID :	10338259
Synonyms :

Safety of [ 450412-27-8 ]

Signal Word:	Warning	Class:
Precautionary Statements:	P261-P280-P301+P312-P302+P352-P305+P351+P338	UN#:
Hazard Statements:	H302-H315-H319-H335	Packing Group:
GHS Pictogram:

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 ]

[ 450412-27-8 ] Synthesis Path-Upstream 1~1

1
[ 450412-27-8 ]
[ 689291-89-2 ]

Reference： [1] Dalton Transactions, 2013, vol. 42, # 2, p. 355 - 358

[ 450412-27-8 ] Synthesis Path-Downstream 1~50

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.

Reference： [1]Current Patent Assignee: ROCHE HOLDING AG - WO2008/55847, 2008, A1 Location in patent: Page/Page column 86-87

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.

Reference： [1]Current Patent Assignee: ROCHE HOLDING AG - WO2008/55847, 2008, A1 Location in patent: Page/Page column 86

4
[ 450412-27-8 ]
[ 689291-89-2 ]

Reference： [1]Dalton Transactions,2013,vol. 42,p. 355 - 358

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

Reference： [1]Barbasiewicz, Michal; Blocki, Krzysztof; Malinska, Maura; Pawlowski, Robert [Dalton Transactions, 2013, vol. 42, # 2, p. 355 - 358]

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

Reference： [1]Barbasiewicz, Michal; Blocki, Krzysztof; Malinska, Maura; Pawlowski, Robert [Dalton Transactions, 2013, vol. 42, # 2, p. 355 - 358]

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;

Reference： [1]Kawamoto, Takuji; Sato, Aoi; Ryu, Ilhyong [Organic Letters, 2014, vol. 16, # 8, p. 2111 - 2113]

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

Reference： [1]Chou, Shu-Hua; Tsai, Chih-Hung; Wu, Chung-Chih; Kumar, Dhirendra; Wong, Ken-Tsung [Chemistry - A European Journal, 2014, vol. 20, # 50, p. 16574 - 16582]

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

Reference： [1]Chou, Shu-Hua; Tsai, Chih-Hung; Wu, Chung-Chih; Kumar, Dhirendra; Wong, Ken-Tsung [Chemistry - A European Journal, 2014, vol. 20, # 50, p. 16574 - 16582]

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

Reference： [1]Chou, Shu-Hua; Tsai, Chih-Hung; Wu, Chung-Chih; Kumar, Dhirendra; Wong, Ken-Tsung [Chemistry - A European Journal, 2014, vol. 20, # 50, p. 16574 - 16582]

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

Reference： [1]Chou, Shu-Hua; Tsai, Chih-Hung; Wu, Chung-Chih; Kumar, Dhirendra; Wong, Ken-Tsung [Chemistry - A European Journal, 2014, vol. 20, # 50, p. 16574 - 16582]

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

Reference： [1]Chou, Shu-Hua; Tsai, Chih-Hung; Wu, Chung-Chih; Kumar, Dhirendra; Wong, Ken-Tsung [Chemistry - A European Journal, 2014, vol. 20, # 50, p. 16574 - 16582]

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

Reference： [1]Chou, Shu-Hua; Tsai, Chih-Hung; Wu, Chung-Chih; Kumar, Dhirendra; Wong, Ken-Tsung [Chemistry - A European Journal, 2014, vol. 20, # 50, p. 16574 - 16582]

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

Reference： [1]Chou, Shu-Hua; Tsai, Chih-Hung; Wu, Chung-Chih; Kumar, Dhirendra; Wong, Ken-Tsung [Chemistry - A European Journal, 2014, vol. 20, # 50, p. 16574 - 16582]

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

Reference： [1]Chou, Shu-Hua; Tsai, Chih-Hung; Wu, Chung-Chih; Kumar, Dhirendra; Wong, Ken-Tsung [Chemistry - A European Journal, 2014, vol. 20, # 50, p. 16574 - 16582]

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

Reference： [1]Chou, Shu-Hua; Tsai, Chih-Hung; Wu, Chung-Chih; Kumar, Dhirendra; Wong, Ken-Tsung [Chemistry - A European Journal, 2014, vol. 20, # 50, p. 16574 - 16582]

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

Reference： [1]Chou, Shu-Hua; Tsai, Chih-Hung; Wu, Chung-Chih; Kumar, Dhirendra; Wong, Ken-Tsung [Chemistry - A European Journal, 2014, vol. 20, # 50, p. 16574 - 16582]

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

Reference： [1]Chou, Shu-Hua; Tsai, Chih-Hung; Wu, Chung-Chih; Kumar, Dhirendra; Wong, Ken-Tsung [Chemistry - A European Journal, 2014, vol. 20, # 50, p. 16574 - 16582]

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

Reference： [1]Chou, Shu-Hua; Tsai, Chih-Hung; Wu, Chung-Chih; Kumar, Dhirendra; Wong, Ken-Tsung [Chemistry - A European Journal, 2014, vol. 20, # 50, p. 16574 - 16582]

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

Reference： [1]Chou, Shu-Hua; Tsai, Chih-Hung; Wu, Chung-Chih; Kumar, Dhirendra; Wong, Ken-Tsung [Chemistry - A European Journal, 2014, vol. 20, # 50, p. 16574 - 16582]

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;

Reference： [1]Chou, Shu-Hua; Tsai, Chih-Hung; Wu, Chung-Chih; Kumar, Dhirendra; Wong, Ken-Tsung [Chemistry - A European Journal, 2014, vol. 20, # 50, p. 16574 - 16582]

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;

Reference： [1]Chou, Shu-Hua; Tsai, Chih-Hung; Wu, Chung-Chih; Kumar, Dhirendra; Wong, Ken-Tsung [Chemistry - A European Journal, 2014, vol. 20, # 50, p. 16574 - 16582]

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

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

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;

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;

28
[ 64-17-5 ]
[ 21740-00-1 ]
[ 450412-27-8 ]

Yield	Reaction Conditions	Operation in experiment
92%	With acetyl chloride In ethanol Reflux;

Reference： [1]Chand-Thakuri, Pratibha; Landge, Vinod G.; Kapoor, Mohit; Young, Michael C. [Journal of Organic Chemistry, 2020, vol. 85, # 10, p. 6626 - 6644]

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;

Reference： [1]Chand-Thakuri, Pratibha; Landge, Vinod G.; Kapoor, Mohit; Young, Michael C. [Journal of Organic Chemistry, 2020, vol. 85, # 10, p. 6626 - 6644]

30
[ 1765-93-1 ]
[ 450412-27-8 ]
C₁₅H₁₂BrFO₂ [ No CAS ]