Name: 181021-20-5|(2-Bromophenethoxy)(tert-butyl)dimethylsilane|98%
Brand: Ambeed
SKU: A656404
Rating: 90 (25 reviews)

1
[ 1074-16-4 ]
[ 18162-48-6 ]
[ 181021-20-5 ]

Yield	Reaction Conditions	Operation in experiment
97%	With 1H-imidazole In N,N-dimethyl-formamide at 0 - 20℃;
90%	With triethylamine In dichloromethane at 25℃; for 12h; Inert atmosphere;
83%	With 1H-imidazole In dichloromethane for 8h;

68%	With 1H-imidazole In dichloromethane at 0℃; for 2h; Inert atmosphere;
68%	With 1H-imidazole In dichloromethane at 0℃; for 2h; Inert atmosphere;	4.1 Step 1: (2-Bromophenethoxy)(tert-butyl)dimethylsilane Add imidazole (6.09g,90mmol) and TBSCl to a solution of 2-(2-bromophenyl)ethane-1-ol (15g,74.6mmol) in dry DCM (80mL) at 0°C under Ar (13.49g,90mmol),and the reaction mixture was stirred at 0°C for 2h. After removing the volatiles under reduced pressure,the residue was purified by silica gel column chromatography (hexane) to obtain the title compound (16 g,68%) as a colorless oil.
	With 1H-imidazole; triethylamine In DMF (N,N-dimethyl-formamide) at 20℃;	8.1; 18 2-(2-bromophenyl)ethanol (5.00 g, 24.87 mmol), tert-butyldimethylsilyl chloride (4.50 g, 29.84 mmol), imidazole (2.54 g, 37.30 mmol), and Et3N (2.09 mL, 12.43 mmol) were mixed together in DMF (50 mL) and left to stir at room temperature overnight. An additional equivalent of tert-butyldimethylsilyl chloride was added and the reaction was essentially complete after one hour. The reaction mixture was diluted with EtOAc and washed with water (3×100 mL). The aqueous phase was then back extracted with EtOAc (1×100 mL). The combined organics were washed with brine (3×100 mL), dried over sodium sulfate, filtered, and concentrated. Silica gel chromatography (20%-70% CH2Cl2/hexanes) gave [2-(2-bromophenyl)ethoxy](tert-butyl)dimethylsilane.
1.2 g	With 1H-imidazole In N,N-dimethyl-formamide at 20℃; for 3h;	40-1.1 Propan-2-yl 2-(2-hydroxyethyl)benzoate (1) Imidazole (677 mg) and tert-butyldimethylchlorosilane (825 mg) were added to a solution of commercially available 2-(2-bromophenyl)ethanol (1.0 g) in N,N-dimethylformamide (8.3 mL), and the mixture was stirred at room temperature for 3 hours. A saturated aqueous solution of ammonium chloride (10 mL) was added to stop the reaction, and the resultant mixture was extracted with diethyl ether. The obtained organic layer was passed through a phase separator, and then concentrated under reduced pressure. The obtained residue was purified by silica gel column chromatography (n-hexane:ethyl acetate = 99:1 to 10:1) to give 2-(2-bromophenyl)ethoxy-tert-butyl-dimethylsilane (1.2 g).
87 mg	With 1H-imidazole In dichloromethane at 20℃; for 2h;
	With 1H-imidazole In dichloromethane at 0 - 20℃; for 5h;

Reference： [1]Feldman, Ken S.; Bruendl, Michelle M.; Schildknegt, Klaas; Bohnstedt, Adolph C. [Journal of Organic Chemistry, 1996, vol. 61, # 16, p. 5440 - 5452]
[2]Li, Kangkang; Li, Jin-Feng; Yin, Bing; Zeng, Fanlong [ChemCatChem, 2022, vol. 14, # 11]
[3]Bell, Russell A.; Dickson, Kieran C.; Valliant, John F. [Canadian Journal of Chemistry, 1999, vol. 77, # 1, p. 146 - 154]
[4]Current Patent Assignee: ASCENTAGEPHARMA GROUP; ASCENTAGE PHARMA SUZHOU; ASCENTAGE PHARMA GROUP CORP - WO2021/139748, 2021, A1 Location in patent: Paragraph 0526-0527
[5]Current Patent Assignee: ASCENTAGEPHARMA GROUP; ASCENTAGE PHARMA SUZHOU; ASCENTAGE PHARMA GROUP CORP - CN113087700, 2021, A Location in patent: Paragraph 0722; 0725-0727
[6]Current Patent Assignee: MERCK & CO INC - US2005/261327, 2005, A1 Location in patent: Page/Page column 19; 28
[7]Current Patent Assignee: TAISHO PHARMACEUTICAL HOLDINGS CO., LTD. - EP3666766, 2020, A1 Location in patent: Paragraph 0966
[8]Langston, Steven P.; Grossman, Stephen; England, Dylan; Afroze, Roushan; Bence, Neil; Bowman, Douglas; Bump, Nancy; Chau, Ryan; Chuang, Bei-Ching; Claiborne, Christopher; Cohen, Larry; Connolly, Kelly; Duffey, Matthew; Durvasula, Nitya; Freeze, Scott; Gallery, Melissa; Galvin, Katherine; Gaulin, Jeffrey; Gershman, Rachel; Greenspan, Paul; Grieves, Jessica; Guo, Jianping; Gulavita, Nanda; Hailu, Shumet; He, Xingyue; Hoar, Kara; Hu, Yongbo; Hu, Zhigen; Ito, Mitsuhiro; Kim, Mi-Sook; Lane, Scott Weston; Lok, David; Lublinsky, Anya; Mallender, William; McIntyre, Charles; Minissale, James; Mizutani, Hirotake; Mizutani, Miho; Molchinova, Nina; Ono, Koji; Patil, Ashok; Qian, Mark; Riceberg, Jessica; Shindi, Vaishali; Sintchak, Michael D.; Song, Keli; Soucy, Teresa; Wang, Yana; Xu, He; Yang, Xiaofeng; Zawadzka, Agatha; Zhang, Ji; Pulukuri, Sai M. [Journal of Medicinal Chemistry, 2021, vol. 64, # 5, p. 2501 - 2520]
[9]Feng, Na; Liang, Qi-Ming; Lu, Si-Yuan; Luo, Lu; Ma, Ai-Jun; Peng, Jin-Bao; Wang, Hong-Mei; Zhang, Xiang-Zhi; Zheng, Jing-Yun [Advanced Synthesis and Catalysis, 2022]

2
[ 17997-47-6 ]
[ 181021-20-5 ]
[ 517883-73-7 ]

Yield	Reaction Conditions	Operation in experiment
82%	With tetrakis(triphenylphosphine) palladium⁽⁰⁾ In toluene at 110℃; for 48h;

Reference： [1]Zhang, Shi-Wei; Swager, Timothy M. [Journal of the American Chemical Society, 2003, vol. 125, # 12, p. 3420 - 3421]

3
[ 181021-20-5 ]
[ 517883-66-8 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: 82 percent / Pd(PPh₃)4 / toluene / 48 h / 110 °C 2: aq. AcOH / tetrahydrofuran

Reference： [1]Zhang, Shi-Wei; Swager, Timothy M. [Journal of the American Chemical Society, 2003, vol. 125, # 12, p. 3420 - 3421]

4
[ 181021-20-5 ]
6,7-dihydro-pyrido[2,1-<i>a</i>]isoquinolinylium; chloride [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: 82 percent / Pd(PPh₃)4 / toluene / 48 h / 110 °C 2: SOCl₂ / acetonitrile / 3 h / 20 °C

Reference： [1]Zhang, Shi-Wei; Swager, Timothy M. [Journal of the American Chemical Society, 2003, vol. 125, # 12, p. 3420 - 3421]

5
[ 181021-20-5 ]
C₁₃H₁₂N⁽¹⁺⁾*C₄H₁₀O₄P^(1-) [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1: 82 percent / Pd(PPh₃)4 / toluene / 48 h / 110 °C 2: aq. AcOH / tetrahydrofuran 3: CD₂Cl₂ / 48 h / 20 °C

Reference： [1]Zhang, Shi-Wei; Swager, Timothy M. [Journal of the American Chemical Society, 2003, vol. 125, # 12, p. 3420 - 3421]

6
[ 181021-20-5 ]
[ 181021-22-7 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 2: 1.) n-BuLi, 2.) hexamethylphosphorous triamide / 1.) THF, hexanes, -78 deg C -> room temperature, 2.) THF, hexanes, -78 deg C -> room temperature 3: 90 percent / n-Bu₄NF / tetrahydrofuran / 2 h / 0 °C

Reference： [1]Feldman, Ken S.; Bruendl, Michelle M.; Schildknegt, Klaas; Bohnstedt, Adolph C. [Journal of Organic Chemistry, 1996, vol. 61, # 16, p. 5440 - 5452]

7
[ 181021-20-5 ]
N-(2-{2-[1-(2,2-Dimethoxy-ethyl)-prop-2-ynyl]-phenyl}-ethyl)-4-methyl-benzenesulfonamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 5 steps 2: 1.) n-BuLi, 2.) hexamethylphosphorous triamide / 1.) THF, hexanes, -78 deg C -> room temperature, 2.) THF, hexanes, -78 deg C -> room temperature 3: 90 percent / n-Bu₄NF / tetrahydrofuran / 2 h / 0 °C 4: 89 percent / diethyl azodicarboxylate, triphenylphosphine / tetrahydrofuran / 10 h / Ambient temperature 5: 85 percent / trimethyl orthoformate, methanol, acetyl chloride / 5 h / Heating

Reference： [1]Feldman, Ken S.; Bruendl, Michelle M.; Schildknegt, Klaas; Bohnstedt, Adolph C. [Journal of Organic Chemistry, 1996, vol. 61, # 16, p. 5440 - 5452]

8
[ 181021-20-5 ]
[ 181021-23-8 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 4 steps 2: 1.) n-BuLi, 2.) hexamethylphosphorous triamide / 1.) THF, hexanes, -78 deg C -> room temperature, 2.) THF, hexanes, -78 deg C -> room temperature 3: 90 percent / n-Bu₄NF / tetrahydrofuran / 2 h / 0 °C 4: 89 percent / diethyl azodicarboxylate, triphenylphosphine / tetrahydrofuran / 10 h / Ambient temperature

Reference： [1]Feldman, Ken S.; Bruendl, Michelle M.; Schildknegt, Klaas; Bohnstedt, Adolph C. [Journal of Organic Chemistry, 1996, vol. 61, # 16, p. 5440 - 5452]

9
[ 4746-97-8 ]
[ 181021-20-5 ]
[ 1056990-63-6 ]

Yield	Reaction Conditions	Operation in experiment
	With tert.-butyl lithium In tetrahydrofuran; pentane at -78℃; for 1h;	8.2; 18 [2-(2-bromophenyl)ethoxy](tert-butyl)dimethylsilane (6.46 g, 20.49 mmol) was dissolved in THF (20 mL) in an oven dried and nitrogen purged flask. The resulting solution was cooled to -78° C. and t-butyl lithium (18.84 mL of a 1.7M solution in pentane) was added dropwise. In a separate oven dried and purged flask, 11 (2.00 g, 12.81 mmol) was dissolved in THF (20 mL) and cooled to -78° C. This solution was then cannulated into the t-butyl lithium solution. After approximately one hour, the reaction was quenched with water (20 mL), warmed to room temperature, and extracted with EtOAc (1×50 mL). The organic phase was washed with water (2×50 mL), and brine (1×50 mL). The combined aqueous layers were back extracted with EtOAc (1×50 mL). The combined organics were dried over sodium sulfate, filtered, and concentrated. Silica gel chromatography, eluting first with 20% CH2Cl2/hexanes then with 65% EtOAc/hexanes gave 8-[2-(2-[tert-butyl(dimethyl)silyl]oxy}ethyl)phenyl]-1,4-dioxaspiro[4.5]decan-8-ol, 39.

Reference： [1]Current Patent Assignee: MERCK & CO INC - US2005/261327, 2005, A1 Location in patent: Page/Page column 19; 28

10
[ 1402599-23-8 ]
[ 181021-20-5 ]
[ 1402599-29-4 ]

Yield	Reaction Conditions	Operation in experiment
	Stage #1: 2-(2-bromophenyl)-O-(tert-butyldimethylsilyl)ethan-2-ol With magnesium; ethylene dibromide In diethyl ether for 1.5h; Reflux; Stage #2: N-(1-benzofuran-2-ylmethylidene)-3,4-dihydro-2H-1,5-benzodioxepine-7-sulfonamide In diethyl ether at 20℃; for 4h; Stage #3: With water; sodium hydrogencarbonate In diethyl ether	16.1 Step 1. A 10 mL round-bottomed flask was charged with (2-(2- bromophenyl)ethoxy)(tert-butyl)dimethylsilane (0.53 g, 1.7 mmol, Combi-Blocks, San Diego, CA), magnesium turnings (0.082 g, 3.4 mmol, Strem, Newburyport, MA), diethyl ether (2.8 mL), and 1 ,2-dibromoethane (0.063 g, 0.34 mmol, Sigma- Aldrich, St. Louis, MO), and then the reaction mixture was heated at reflux for 90 min. After that time, the reaction mixture was cooled to room temperature and transferred by syringe to a mixture of N-(l-benzofuran-2-ylmethylidene)-3,4- dihydro-2H-l,5-benzodioxepine-7-sulfonamide (intermediate A)(0.10 g, 0.28 mmol) and diethyl ether (2.8 mL), and then the reaction mixture was stirred for 4 h. After that time, saturated aqueous sodium bicarbonate (5.0 mL) was added, the mixture was partitioned between ethyl acetate (50 mL) and saturated aqueous sodium bicarbonate (50 mL), the layers were separated, the organic material was washed sequentially with saturated aqueous sodium bicarbonate (50 mL) and brine (50 mL), dried (sodium sulfate), filtered, and the filtrate was concentrated. The isolated material (0.83 g) was used in the next step of the synthesis without purification.

Reference： [1]Current Patent Assignee: AMGEN INC - WO2012/138776, 2012, A1 Location in patent: Page/Page column 98

11
[ 181021-20-5 ]
C₁₂H₁₂BrCl [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1.1: diisobutylaluminium hydride / hexane / 2 h / 0 - 55 °C / Inert atmosphere 1.2: XPhos-OMs (G₃) precatalyst / 20 °C 2.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 20 °C 3.1: carbon tetrabromide; triphenylphosphine / dichloromethane / 0.5 h / 0 - 20 °C