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[ CAS No. 84750-93-6 ] {[proInfo.proName]}

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Product Details of [ 84750-93-6 ]

CAS No. :84750-93-6 MDL No. :MFCD08276320
Formula : C8H5BrF2 Boiling Point : -
Linear Structure Formula :- InChI Key :-
M.W : 219.03 Pubchem ID :-
Synonyms :

Safety of [ 84750-93-6 ]

Signal Word:Danger Class:8
Precautionary Statements:P280-P305+P351+P338-P310 UN#:3265
Hazard Statements:H227-H314 Packing Group:
GHS Pictogram:

Application In Synthesis of [ 84750-93-6 ]

* 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.

  • Downstream synthetic route of [ 84750-93-6 ]

[ 84750-93-6 ] Synthesis Path-Downstream   1~54

  • 1
  • [ 84750-93-6 ]
  • [ 155820-88-5 ]
YieldReaction ConditionsOperation in experiment
92% With potassium fluoride; 18-crown-6 ether In N,N-dimethyl-formamide at 70℃; for 4h;
64 %Spectr. With potassium fluoride; 18-crown-6 ether In water; N,N-dimethyl-formamide at 80 - 140℃; sealed tube;
  • 2
  • [ 895164-12-2 ]
  • [ 84750-93-6 ]
YieldReaction ConditionsOperation in experiment
70% With disodium hydrogenphosphate; sodium amalgam In methanol at -40 - 0℃; for 1h;
  • 3
  • [ 1895-39-2 ]
  • [ 1122-91-4 ]
  • [ 84750-93-6 ]
YieldReaction ConditionsOperation in experiment
82% With triphenylphosphine In N,N-dimethyl-formamide at 100℃; for 1h; Inert atmosphere;
82% With triphenylphosphine In N,N-dimethyl-formamide at 110℃; for 2h;
82% With triphenylphosphine In N,N-dimethyl-formamide at 100℃; for 0.5h; General Procedure for synthesis of gem-difluoroalkenes General procedure: Aromatic aldehyde (5.0 mmol), PPh3 (1.57 g, 6.50 mmol) and DMF (5.0 mL) wereplaced into an round-bottomed flask that equipped with a stirring bar. The reactionwas stirring at 100 oC. ClCF2CO2Na (1.14 g, 7.50 mmol) was dissolved in DMF (3.0mL) and the solution was injected into reaction slowly with CO2 release. The mixturewas stirring at 100 oC for 30 min and then cooled to room temperature and quenchedby the addition of H2O. The mixture was extracted by diethyl ether (50 mL × 3),washed with saturated brine twice and combined organic extracts were dried overNa2SO4, filled and concentrated in vacuo. The residue was purified by flashchromatography on silica gel.
74% With triphenylphosphine In N,N-dimethyl-formamide at 110℃; Inert atmosphere;
73% With triphenylphosphine In 1-methyl-pyrrolidin-2-one at 120℃; Inert atmosphere;
65% With triphenylphosphine In 1-methyl-pyrrolidin-2-one at 100℃; Inert atmosphere; Schlenk technique;
56% With triphenylphosphine In N,N-dimethyl-formamide at 100℃; for 0.5h;
With triphenylphosphine In diethylene glycol dimethyl ether at 180℃;
With triphenylphosphine In 1-methyl-pyrrolidin-2-one at 100℃; for 0.0833333h; Inert atmosphere;
With triphenylphosphine In 1-methyl-pyrrolidin-2-one at 100℃; for 0.5h; Inert atmosphere;
With triphenylphosphine In N,N-dimethyl-formamide at 100℃; for 5h; Inert atmosphere;
With triphenylphosphine In N,N-dimethyl-formamide at 100℃; for 1h;
With triphenylphosphine In N,N-dimethyl-formamide at 100℃;
With triphenylphosphine In N,N-dimethyl-formamide at 100℃; for 0.5h;
With triphenylphosphine In N,N-dimethyl-formamide at 110℃;

Reference: [1]Sakaguchi, Hironobu; Uetake, Yuta; Ohashi, Masato; Niwa, Takashi; Ogoshi, Sensuke; Hosoya, Takamitsu [Journal of the American Chemical Society, 2017, vol. 139, # 36, p. 12855 - 12862]
[2]Liu, Jiawang; Yang, Ji; Ferretti, Francesco; Jackstell, Ralf; Beller, Matthias [Angewandte Chemie - International Edition, 2019, vol. 58, # 14, p. 4690 - 4694][Angew. Chem., 2019, vol. 131, # 14, p. 4738 - 4742,5]
[3]Huang, Weichen; Shen, Qilong; Xiao, Yisa [Chinese Chemical Letters, 2022]
[4]Zhang, Jun-Qi; Hu, Dandan; Song, Jinyu; Ren, Hongjun [Journal of Organic Chemistry, 2021, vol. 86, # 6, p. 4646 - 4660]
[5]Fang, Zheng; Hu, Wen-Li; Liu, De-Yong; Yu, Chu-Yi; Hu, Xiang-Guo [Green Chemistry, 2017, vol. 19, # 5, p. 1299 - 1302]
[6]Loska, Rafal; Szachowicz, Katarzyna; Szydlik, Dorota [Organic Letters, 2013, vol. 15, # 22, p. 5706 - 5709]
[7]Tian, Hao; Xia, Qing; Wang, Qiang; Dong, Jianyang; Liu, Yuxiu; Wang, Qingmin [Organic Letters, 2019, vol. 21, # 12, p. 4585 - 4589]
[8]Lin, Shaw-Tao; Lee, Chuan-Chen; Wu, En-Chien [Tetrahedron, 2008, vol. 64, # 22, p. 5103 - 5106]
[9]Cai, Sai-Hu; Ye, Lu; Wang, Ding-Xing; Wang, Yi-Qiu; Lai, Lin-Jie; Zhu, Chuan; Feng, Chao; Loh, Teck-Peng [Chemical Communications, 2017, vol. 53, # 62, p. 8731 - 8734]
[10]Liu, Haidong; Ge, Liang; Wang, Ding-Xing; Chen, Nan; Feng, Chao [Angewandte Chemie - International Edition, 2019, vol. 58, # 12, p. 3918 - 3922][Angew. Chem., 2019, vol. 131, # 12, p. 3958 - 3962,5]
[11]Kondoh, Azusa; Koda, Kazumi; Terada, Masahiro [Organic Letters, 2019, vol. 21, # 7, p. 2277 - 2280]
[12]Zhang, Qi-Qi; Chen, Shi-Yong; Lin; Wang, Honggen; Li, Qingjiang [Organic Letters, 2019, vol. 21, # 9, p. 3123 - 3126]
[13]Wang, Qiang; Qu, Yi; Tian, Hao; Liu, Yuxiu; Song, Hongjian; Wang, Qingmin [Chemistry - A European Journal, 2019, vol. 25, # 37, p. 8686 - 8690]
[14]Song, Shengjin; Liu, Huan; Wang, Lu; Zhu, Chuan; Loh, Teck-Peng; Feng, Chao [Chinese Journal of Chemistry, 2019, vol. 37, # 10, p. 1036 - 1040]
[15]Jiang, Xinpeng; Wang, Guan; Zheng, Zicong; Yu, Xiaohui; Hong, Ye; Xia, Haoqi; Yu, Chuanming [Organic Letters, 2020, vol. 22, # 24, p. 9762 - 9766]
  • 4
  • [ 1219454-89-3 ]
  • [ 1122-91-4 ]
  • [ 142-08-5 ]
  • [ 84750-93-6 ]
YieldReaction ConditionsOperation in experiment
72% Stage #1: 2-((difluoromethyl)sulfonyl)pyridine; 4-bromo-benzaldehyde With potassium <i>tert</i>-butylate In N,N-dimethyl-formamide at -50 - -40℃; for 0.25h; Inert atmosphere; Stage #2: With hydrogenchloride; water; ammonium chloride In N,N-dimethyl-formamide at -40 - 60℃; Inert atmosphere;
  • 5
  • [ 1258013-09-0 ]
  • [ 84750-93-6 ]
YieldReaction ConditionsOperation in experiment
77% With lithium hexamethyldisilazane In tetrahydrofuran at 0℃; Inert atmosphere;
  • 6
  • [ 93102-05-7 ]
  • [ 84750-93-6 ]
  • [ 1381980-30-8 ]
YieldReaction ConditionsOperation in experiment
80% With lithium fluoride In acetonitrile at 60℃; for 6h;
With lithium fluoride In acetonitrile at 20℃; for 17h; Inert atmosphere; 57 To a a solution of l-bromo-4-(2,2-difluorovinyl)benzene (1.14 g, 5.2 mmol) in acetonitrile (10 mL) was added N-benzyl-l-methoxy-N-((trimethylsilyl)methyl)methanamine (2.0 mL, 7.8 mmol) and lithium fluoride (263 mg, 10.1 mmol). The reaction vessel was purged with argon, sealed, and sonicated at room temperature for 17 hours. The crude reaction mixture was filtered to remove the inorganic salts and concentrated to dryness then purified by silica gel chromatography (0-40 % ethyl acetate/hexanes) to give l-benzyl-4-(4- bromophenyl)-3,3-difluoropyrrolidine as a colorless, semi-viscous liquid
  • 7
  • [ 680-15-9 ]
  • [ 1122-91-4 ]
  • [ 84750-93-6 ]
YieldReaction ConditionsOperation in experiment
70% With triphenylphosphine; potassium iodide In acetonitrile at 70℃; for 4h; Inert atmosphere; Typical procedure for preparation of 1,1-difluoroalkenes A 250 mL, three necked round bottomed flask was equipped with a stir bar. The vessel was then fitted with a condenser topped by a T-tube with slow flow of N2, and then sealed with septa. The vessel was flamed dried and then allowed to cool to room temperature. Under the inert, nitrogen atmosphere, acetonitrile (75 mL) was added to the vessel, and the temperature was increased to 70 °C. Then triphenylphosphine (34.5 g, 135 mmol, 3 equiv.), potassium iodide (15.0 g, 90 mmol, 2 equiv.), and 4-bromobenzaldehyde (9.80 g, 45 mmol, 1 equiv.) were added and let stir for 30 min. Methyl 2,2-difluoro-2-(fluorosulfonyl)acetate (MDFA) (19.7 g, 78.75 mmol,1.75 equiv.) was then added slowly over a period 1 h. The resulting mixture was stirred for three hours, a nitrogen atmosphere being maintained until the end of the reaction. Then the reaction was quenched with water and extracted with ethyl acetate. Trifluorotoluene (15 mmol) was added as internal standard and the yield of the crude reaction was measured by 19F NMR (72%). The ethyl acetate was then removed by rotary evaporation to produce a black, semi-solid slurry. Product was isolated from the slurry and separated from residual triphenylphosphine by extraction 5 times with hexane (100 mL). The combined hexane extracts were combined and concentrated. Additional impurities were removed via column chromatography using a 95:5 mixture of hexanes:methylene chloride to obtain pure product: (6.9 g (70%), clear liquid; 1H NMR δ 7.48 (d, J = 9.1 Hz, 2H), 7.21 (d, J = 8.1 Hz, 2H), 5.25 (dd, J = 25 Hz, J = 3.1 Hz, 1H); 19F NMR δ -81.8 (dd, J = 30 Hz, J = 27 Hz, 1F), -83.7 (dd, J = 29 Hz, J = 3.8 Hz, 1F).
Stage #1: 4-bromo-benzaldehyde With triphenylphosphine; potassium iodide In acetonitrile at 70℃; for 0.5h; Inert atmosphere; Stage #2: 2,2-difluoro-2-(fluorosulfonyl)acetate In acetonitrile at 70℃; for 3.5h; Inert atmosphere;
  • 8
  • [ 1122-91-4 ]
  • 2,2‐difluoro‐2‐(triphenylphosphonio)acetate [ No CAS ]
  • [ 84750-93-6 ]
YieldReaction ConditionsOperation in experiment
90% In 1-methyl-pyrrolidin-2-one at 60℃; for 1h; Sealed tube; 13 In a 5 mL sealed tube, a solution of triphenyl difluoromethylidene phosphonium salt (0.57 g, 1.6 mmol)And p-bromobenzaldehyde (148 mg, 0.8 mmol) were dissolved in N-methylpyrrolidone,At 60 , the tube closure reaction 1h. Then the heating was stopped. After the reaction was allowed to cool, the product was isolated by column chromatography (petroleum ether) after extraction with water and ether. The yield (157.7 mg) was obtained in a yield of 90%.
89% In 1-methyl-pyrrolidin-2-one at 80℃; for 4h; Inert atmosphere; Schlenk technique;
  • 9
  • [ 1613-37-2 ]
  • [ 84750-93-6 ]
  • [ 1379771-31-9 ]
YieldReaction ConditionsOperation in experiment
46% Stage #1: Quinoline N-oxide; 1,1-difluoro-2-(4-bromophenyl)ethene In toluene at 80℃; for 48h; Inert atmosphere; Stage #2: With water
  • 10
  • [ 84750-93-6 ]
  • [ 55738-12-0 ]
  • 1-benzyl-4,5-dimethyl-2-(4-bromobenzyl)imidazole [ No CAS ]
YieldReaction ConditionsOperation in experiment
65% With water In tetrahydrofuran at 70℃; for 48h; Inert atmosphere;
  • 11
  • [ 1600503-70-5 ]
  • [ 1122-91-4 ]
  • [ 84750-93-6 ]
YieldReaction ConditionsOperation in experiment
90% Stage #1: potassium 2-pyridinyl sulfonyl-difluoroacetate; 4-bromo-benzaldehyde In N,N-dimethyl-formamide at 40℃; for 2h; Stage #2: With hydrogenchloride; ammonium chloride In N,N-dimethyl-formamide at 40℃; for 2h;
90% Stage #1: potassium 2-pyridinyl sulfonyl-difluoroacetate; 4-bromo-benzaldehyde In N,N-dimethyl-formamide at 40℃; for 2h; Stage #2: With hydrogenchloride; ammonium chloride In water; N,N-dimethyl-formamide at 40℃; for 2h;
  • 12
  • [ 115262-00-5 ]
  • [ 1122-91-4 ]
  • [ 84750-93-6 ]
YieldReaction ConditionsOperation in experiment
53% With triphenylphosphine In tetrahydrofuran at 70℃; for 10h; Sealed tube; Typical procedures: General procedure: To a solution of 1-naphthaldehyde (1a)( 78 mg, 0.5 mmol) in THF (2 mL), Me3SiCF2Cl 237 1.5 and triphenylphosphine (393 mg, 15 mmol) were added at room temperature. The reaction tube was sealed, and the mixture was heated to 70 °C and stirred for 10 h. The reaction was quenched with water (5 mL), then extracted with Et2O (20 mL) twice, the combined organic phase was dried over MgSO4. After the removal of solvents under vacuum, the crude product was further purified by silica gel column chromatography to give product 2a as a colorless liquid. Yield: 59% (56 mg).
  • 13
  • [ 58310-28-4 ]
  • [ 1122-91-4 ]
  • [ 84750-93-6 ]
YieldReaction ConditionsOperation in experiment
70% With 1,8-diazabicyclo[5.4.0]undec-7-ene; In N,N-dimethyl-formamide; at 50℃; for 4h;Inert atmosphere; General procedure: Into the mixture of difluoromethyltriphenylphosphoniumbromide (236 mg, 0.6 mmol), aldehyde (0.2 mmol) and DBU(90 mL, 0.6 mmol) was added DMF (2 mL) under N2. The resulting mixture was stirred at 50 C for 4 h. After being cooled to room temperature, the solution was diluted with CH2Cl2 (10 mL) andwashed with water (5 mL x 2). The organic phase was dried over sodium sulfate. The solvent was removed by concentration and the residue was subjected to column chromatography to give the pure product.
  • 14
  • [ 371-67-5 ]
  • [ 5467-74-3 ]
  • [ 84750-93-6 ]
  • [ 155820-88-5 ]
YieldReaction ConditionsOperation in experiment
75% With ammonium chloride; lithium hydroxide at 100℃; for 24h; Schlenk technique;
  • 15
  • [ 59625-59-1 ]
  • 2,2‐difluoro‐2‐(triphenylphosphonio)acetate [ No CAS ]
  • [ 84750-93-6 ]
YieldReaction ConditionsOperation in experiment
59 %Spectr. In para-xylene at 100℃; for 1h; Inert atmosphere; Typical procedure for the synthesis of gem-difluorostyrenes General procedure: A dried Schlenk tube was charged with 2 (0.2 mmol), Ph3P (63 mg, 0.24 mmol) and p-xylene (2 mL) under N2. The resulting mixture was stirred at 120 °C for 6 h. After being cooled to room temperature, tBuOK (40 mg, 0.36 mmol) and p-xylene (0.5 mL) were added into the mixture under N2 and stirred at room temperature for 15 min. PDFA (143 mg, 0.4 mmol) and p-xylene (0.5 mL) were added into the solution under N2 and stirred at 100 °C for another 1 h. After being cooled to room temperature, the mixture was subjected to flash column chromatography to afford the pure product
  • 16
  • [ 81290-20-2 ]
  • [ 1122-91-4 ]
  • [ 84750-93-6 ]
YieldReaction ConditionsOperation in experiment
87% With triphenylphosphine; lithium iodide In 1,4-dioxane; N,N-dimethyl-formamide at 120℃; for 24h; Sealed tube; Glovebox; Inert atmosphere;
  • 17
  • [ 1008-89-5 ]
  • [ 84750-93-6 ]
  • (Z)-2-(2-(2-(4-bromophenyl)-1-fluorovinyl)phenyl)pyridine [ No CAS ]
YieldReaction ConditionsOperation in experiment
90% With [Cp*Co(MeCN)3](SbF6)2; calcium hydroxide at 25℃; for 24h; Inert atmosphere; Glovebox;
  • 18
  • [ 221044-05-9 ]
  • [ 84750-93-6 ]
  • (Z)-2-(2-(4-bromophenyl)-1-fluorovinyl)-1-(pyrimidin-2-yl)-1H-indole [ No CAS ]
YieldReaction ConditionsOperation in experiment
99% With [Cp*Co(MeCN)3](SbF6)2; calcium hydroxide at 45℃; for 24h; Inert atmosphere; Glovebox;
  • 19
  • [ 1610855-35-0 ]
  • [ 84750-93-6 ]
  • (Z)-2-(2-(4-bromophenyl)-1-fluorovinyl)-4-methoxy-1-(pyrimidin-2-yl)-1H-indole [ No CAS ]
YieldReaction ConditionsOperation in experiment
95% With [Cp*Co(MeCN)3](SbF6)2; calcium hydroxide at 45℃; for 24h; Inert atmosphere; Glovebox;
  • 20
  • [ 1451369-26-8 ]
  • [ 84750-93-6 ]
  • (Z)-4-(benzyloxy)-2-(2-(4-bromophenyl)-1-fluorovinyl)-1-(pyrimidin-2-yl)-1H-indole [ No CAS ]
YieldReaction ConditionsOperation in experiment
94% With [Cp*Co(MeCN)3](SbF6)2; calcium hydroxide at 45℃; for 24h; Inert atmosphere; Glovebox;
  • 21
  • [ 1562408-61-0 ]
  • [ 84750-93-6 ]
  • methyl (Z)-2-(2-(4-bromophenyl)-1-fluorovinyl)-1-(pyrimidin-2-yl)-1H-indole-4-carboxylate [ No CAS ]
YieldReaction ConditionsOperation in experiment
96% With [Cp*Co(MeCN)3](SbF6)2; calcium hydroxide at 45℃; for 24h; Inert atmosphere; Glovebox;
  • 22
  • [ 1414866-89-9 ]
  • [ 84750-93-6 ]
  • (Z)-2-(2-(4-bromophenyl)-1-fluorovinyl)-4-chloro-1-(pyrimidin-2-yl)-1H-indole [ No CAS ]
YieldReaction ConditionsOperation in experiment
88% With [Cp*Co(MeCN)3](SbF6)2; calcium hydroxide at 45℃; for 24h; Inert atmosphere; Glovebox;
  • 23
  • 4-bromo-1-(pyrimidin-2-yl)-1H-indole [ No CAS ]
  • [ 84750-93-6 ]
  • C20H12Br2FN3 [ No CAS ]
YieldReaction ConditionsOperation in experiment
90% With [Cp*Co(MeCN)3](SbF6)2; calcium hydroxide at 45℃; for 24h; Inert atmosphere; Glovebox;
  • 24
  • [ 1414866-81-1 ]
  • [ 84750-93-6 ]
  • (Z)-2-(2-(4-bromophenyl)-1-fluorovinyl)-5-methyl-1-(pyrimidin-2-yl)-1H-indole [ No CAS ]
YieldReaction ConditionsOperation in experiment
95% With [Cp*Co(MeCN)3](SbF6)2; calcium hydroxide at 45℃; for 24h; Inert atmosphere; Glovebox;
  • 25
  • [ 1310708-88-3 ]
  • [ 84750-93-6 ]
  • (Z)-2-(2-(4-bromophenyl)-1-fluorovinyl)-5-methoxy-1-(pyrimidin-2-yl)-1H-indole [ No CAS ]
YieldReaction ConditionsOperation in experiment
91% With [Cp*Co(MeCN)3](SbF6)2; calcium hydroxide at 45℃; for 24h; Inert atmosphere; Glovebox;
  • 26
  • [ 1414866-87-7 ]
  • [ 84750-93-6 ]
  • methyl (Z)-2-(2-(4-bromophenyl)-1-fluorovinyl)-1-(pyrimidin-2-yl)-1H-indole-5-carboxylate [ No CAS ]
YieldReaction ConditionsOperation in experiment
97% With [Cp*Co(MeCN)3](SbF6)2; calcium hydroxide at 45℃; for 24h; Inert atmosphere; Glovebox;
  • 27
  • [ 1380503-24-1 ]
  • [ 84750-93-6 ]
  • (Z)-2-(2-(4-bromophenyl)-1-fluorovinyl)-5-fluoro-1-(pyrimidin-2-yl)-1H-indole [ No CAS ]
YieldReaction ConditionsOperation in experiment
98% With [Cp*Co(MeCN)3](SbF6)2; calcium hydroxide at 45℃; for 24h; Inert atmosphere; Glovebox;
  • 28
  • [ 1380503-25-2 ]
  • [ 84750-93-6 ]
  • (Z)-2-(2-(4-bromophenyl)-1-fluorovinyl)-5-chloro-1-(pyrimidin-2-yl)-1H-indole [ No CAS ]
YieldReaction ConditionsOperation in experiment
91% With [Cp*Co(MeCN)3](SbF6)2; calcium hydroxide at 45℃; for 24h; Inert atmosphere; Glovebox;
  • 29
  • [ 1414866-82-2 ]
  • [ 84750-93-6 ]
  • (Z)-2-(2-(4-bromophenyl)-1-fluorovinyl)-6-methyl-1-(pyrimidin-2-yl)-1H-indole [ No CAS ]
YieldReaction ConditionsOperation in experiment
98% With [Cp*Co(MeCN)3](SbF6)2; calcium hydroxide at 45℃; for 24h; Inert atmosphere; Glovebox;
  • 30
  • [ 1380503-28-5 ]
  • [ 84750-93-6 ]
  • (Z)-2-(2-(4-bromophenyl)-1-fluorovinyl)-6-fluoro-1-(pyrimidin-2-yl)-1H-indole [ No CAS ]
YieldReaction ConditionsOperation in experiment
95% With [Cp*Co(MeCN)3](SbF6)2; calcium hydroxide at 45℃; for 24h; Inert atmosphere; Glovebox;
  • 31
  • [ 1380503-29-6 ]
  • [ 84750-93-6 ]
  • (Z)-2-(2-(4-bromophenyl)-1-fluorovinyl)-6-chloro-1-(pyrimidin-2-yl)-1H-indole [ No CAS ]
YieldReaction ConditionsOperation in experiment
97% With [Cp*Co(MeCN)3](SbF6)2; calcium hydroxide at 45℃; for 24h; Inert atmosphere; Glovebox;
  • 32
  • [ 1310708-87-2 ]
  • [ 84750-93-6 ]
  • (Z)-2-(2-(4-bromophenyl)-1-fluorovinyl)-7-ethyl-1-(pyrimidin-2-yl)-1H-indole [ No CAS ]
YieldReaction ConditionsOperation in experiment
98% With [Cp*Co(MeCN)3](SbF6)2; calcium hydroxide at 45℃; for 24h; Inert atmosphere; Glovebox;
  • 33
  • [ 1451369-28-0 ]
  • [ 84750-93-6 ]
  • (Z)-2-(2-(4-bromophenyl)-1-fluorovinyl)-1-(5-fluoropyrimidin-2-yl)-1H-indole [ No CAS ]
YieldReaction ConditionsOperation in experiment
98% With [Cp*Co(MeCN)3](SbF6)2; calcium hydroxide at 45℃; for 24h; Inert atmosphere; Glovebox;
  • 34
  • [ 66318-88-5 ]
  • [ 84750-93-6 ]
  • (Z)-2-(3-(2-(4-bromophenyl)-1-fluorovinyl)naphthalen-2-yl)pyridine [ No CAS ]
YieldReaction ConditionsOperation in experiment
95% With [Cp*Co(MeCN)3](SbF6)2; calcium hydroxide at 25℃; for 24h; Inert atmosphere; Glovebox;
  • 35
  • [ 2885-00-9 ]
  • [ 84750-93-6 ]
  • (Z)-(2-(4-bromophenyl)-1-fluorovinyl)(octadecyl)sulfane [ No CAS ]
  • (E)-(2-(4-bromophenyl)-1-fluorovinyl)(octadecyl)sulfane [ No CAS ]
  • 36
  • [ 17643-17-3 ]
  • [ 84750-93-6 ]
  • (Z)-2-(2-((2-(4-bromophenyl)-1-fluorovinyl)thio)ethoxy)ethan-1-ol [ No CAS ]
  • (E)-2-(2-((2-(4-bromophenyl)-1-fluorovinyl)thio)ethoxy)ethan-1-ol [ No CAS ]
YieldReaction ConditionsOperation in experiment
81.818 % de With 1,3-bis-(2,6-diisopropylphenyl)-imidazol-2-ylidene In acetonitrile at 20℃; for 10h; Inert atmosphere; Molecular sieve; Overall yield = 95 %; Overall yield = 61.1 mg; diastereoselective reaction;
  • 37
  • [ 1432484-52-0 ]
  • [ 84750-93-6 ]
  • 3-(4-(benzyloxy)benzyl)-6-(4-bromobenzyl)-1,2,4,5-tetrazine [ No CAS ]
YieldReaction ConditionsOperation in experiment
85% Stage #1: 1-(benzyloxy)-4-(2,2-difluorovinyl)benzene With hydrazine In water; N,N-dimethyl-formamide at 20℃; Green chemistry; Stage #2: 1,1-difluoro-2-(4-bromophenyl)ethene With hydrazine In water; N,N-dimethyl-formamide at 20℃; Green chemistry; Stage #3: With potassium carbonate In water; ethyl acetate at 20℃; for 24h; Green chemistry;
85% Stage #1: 1-(benzyloxy)-4-(2,2-difluorovinyl)benzene; 1,1-difluoro-2-(4-bromophenyl)ethene With hydrazine hydrate In N,N-dimethyl-formamide Stage #2: With potassium carbonate In water; ethyl acetate for 24h; 6 Example 6 A solution of 1- (benzyloxy) -4- (2,2-difluorovinyl) benzene (27 mg, 0.11 mmol, 1 equiv) in DMF (3 mL) was added hydrazine hydrate (80%, 19 mg, 0.55 mmol, 5 equiv) was stirred for 2-4 hours and then 1,1-difluoro-2- (4-bromophenyl) ethylene (206 mg, 1.1 mmol, 10 equiv) was added to the other reaction flask, Add DMF (3 mL) and add hydrazine hydrate (80%, 190 mg, 0.55 mmol, 50 equiv) for 2-4 hours; The two were mixed directly after the end of the reaction, co-processing, adding 3mL saturated ammonium chloride quenching, and then extracted with 5mL dichloromethane three times, separated to get the organic phase; The organic phase was dried over anhydrous magnesium sulfate, suction filtered, and the organic phase was dried to give a white or violet solid which was dissolved with ethyl acetate and saturated potassium carbonate solution, The reaction was carried out in air for 24 hours. After completion of the reaction, the organic phase was directly partitioned to give an organic phase which was dried over anhydrous sodium sulfate, The filtrate was distilled under reduced pressure and then separated by silica gel flash column chromatography. The filtrate was distilled under reduced pressure and separated by silica gel flash column chromatography to give the target product compound 14 (18 mg, 0.05 mmol).
  • 38
  • [ 1013-88-3 ]
  • [ 84750-93-6 ]
  • 4-(2,2-difluorovinyl)-N-(diphenylmethylene)aniline [ No CAS ]
YieldReaction ConditionsOperation in experiment
790 mg With tris-(dibenzylideneacetone)dipalladium(0); sodium t-butanolate; XPhos In toluene at 100℃; for 3h; 13.A (A) 4-(2,2-difluorovinyl)-N-(diphenylmethylene)aniline (A) 4-(2,2-difluorovinyl)-N-(diphenylmethylene)aniline (0289) To a mixture of 1-bromo-4-(2,2-difluorovinyl)benzene (0.32 mL), 2-dicyclohexylphosphino-2',4',6'-triisopropyl-1,1'-biphenyl (220 mg), diphenylmethanimine (0.76 mL), sodium tert-butoxide (440 mg) and toluene (10 mL) was added tris(dibenzylideneacetone)dipalladium(0) (210 mg). The reaction mixture was stirred at 100 °C for 3 hr and cooled to room temperature. Water was added, and the mixture was extracted with ethyl acetate. The extract was washed with water and saturated brine, and dried over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure and the obtained residue was purified by silica gel column chromatography (ethyl acetate/methanol) to give the title compound (790 mg).
  • 39
  • [ 89295-32-9 ]
  • [ 84750-93-6 ]
  • C14H14BrF3O2 [ No CAS ]
YieldReaction ConditionsOperation in experiment
51% With triethylamine tris(hydrogen fluoride); 9-(2-mesityl)-10-methylacridinium perchlorate In acetonitrile at 20℃; for 96h; Inert atmosphere; Schlenk technique; Irradiation;
With triethylamine tris(hydrogen fluoride); 9-(2-mesityl)-10-methylacridinium perchlorate In acetonitrile for 96h; Inert atmosphere; Irradiation; 2.1; 2.2 Example 2 (1) 1.0 mmol of 1-(β,β-difluorovinyl)4-bromobenzene, 3.0 mmol of ethyl 2-[(phenylsulfonyl)methyl]acrylate 2.0 mmol of triethyl argon under an argon atmosphere Amine trihydrofluoride, 0.002 mmol of 9-mesityl-10-methyl acridine perchlorate was sequentially added to 1.0 mL of acetonitrile to obtain a mixture;(2) Under an argon atmosphere,The mixture is at a wavelength of 450 nm at a light source,The reaction was carried out for 96 hours under a blue light of an intensity of 8 W LED, and high allyl trifluoromethyl compound 2 was collected from the reaction product.
  • 40
  • [ 31469-15-5 ]
  • [ 84750-93-6 ]
  • (Z)-methyl 4-(4-bromophenyl)-3-fluoro-2,2-dimethylbut-3-enoate [ No CAS ]
YieldReaction ConditionsOperation in experiment
84% With phosphazene base-P4-tert-butyl In hexane; toluene at 20℃; for 13h; Inert atmosphere; stereoselective reaction;
  • 41
  • ethyl 2-benzyl-5-methylhexa-2,3-dienoate [ No CAS ]
  • [ 84750-93-6 ]
  • ethyl (Z)-2-benzyl-2-(2-(4-bromophenyl)-1-fluorovinyl)-5-methylhex-3-ynoate [ No CAS ]
YieldReaction ConditionsOperation in experiment
58% With lithium tert-butoxide In dimethyl sulfoxide at 20℃; for 1h; Inert atmosphere; stereoselective reaction;
  • 42
  • [ 1122-91-4 ]
  • [ 87189-16-0 ]
  • [ 84750-93-6 ]
YieldReaction ConditionsOperation in experiment
With triphenylphosphine; In 1-methyl-pyrrolidin-2-one; at 100℃;Sealed tube; Inert atmosphere; General procedure: An oven-dried 3-neck round-bottomed ask equipped with amagnetic stir bar was charged with aryl aldehyde (1.0 equiv.) andtriphenylphosphine (1.2 or 1.5 equiv.). The system was sealed withthree PFTE septa, and subsequently evacuated and backlled withN2 three times. Dry NMP was added via syringe transfer (PTFE sy-ringe with oven-dried stainless-steel needle), and the system wasimmersed in a preheated 100C oil bath. Once no solid reagentsremained (approximately 2 min of heating), potassium bromodi-uoroacetate (1.5 or 1.8 equiv.) was added portionwise over 0.5 h,with the rate of addition controlling the evolution of CO2 gas. Onceall of the potassium bromodiuoroacetate was added, the solutionwas allowed to stir for 0.5e1 h. Upon completion, the reaction wascooled to room temperature and then quenched with H2O. Subse-quently, Et2O was added to the reaction, and the mixture waswashed with H2O (ve times), and the aqueous layer was back-extracted with Et2O (two times). The combined organic layerswere dried over Na2SO4 and concentrated. The crude material wasdry-packed onto silica gel and then eluted through a plug of silicagel with EtOAc:hexanes (1:1) to remove triphenylphosphine oxide.Subsequently, H2O2 (30% in H2O) was added to the mother liquorand allowed to react for 30 min to oxidize the residual triphenyl-phosphine. The organic layer was washed with H2O (three times),dried over Na2SO4, concentrated, and subjected to normal phaseash chromatography using EtOAc and hexanes.
  • 43
  • [ 84750-93-6 ]
  • [ 120-83-2 ]
  • 1-(2-(4-bromophenyl)-1,1-difluoroethoxy)-2,4-dichlorobenzene [ No CAS ]
  • C14H8BrCl2FO [ No CAS ]
YieldReaction ConditionsOperation in experiment
59% With 1,3,4,6,7,8-hexahydro-2H-pyrimido[1,2-a]pyrimidine In water; 1,2-dichloro-benzene at 140℃; for 24h; Glovebox; Sealed tube; Inert atmosphere; regioselective reaction; 5.4. General procedure for the organocatalyzed addition of phenolsto gem-difluoroalkenes (B-2) General procedure: An oven-dried one-dram vial equipped with a magnetic stir barwas charged with 1 equivalent of diuoroalkene and 3 equivalentsof phenol. The system was brought into a glovebox, and 0.5equivalents of TBD were added. Dry DCB (0.9 mL) was added viasyringe transfer (PTFE syringe with oven-dried stainless-steelneedle), and the vial was sealed with a screw-top cap containing aPTFE-lined septum. The system was removed from the glovebox,and distilled H2O (0.1 mL, distilled under N2 to remove dissolvedO2) was added via syringe transfer (PTFE syringe with oven-driedstainless-steel needle) under N2. The reaction was placed within aheating mantle preheated to 140C and stirred for 24 h. The reac-tion was cooled to room temperature, and then standardized by adding 50 m L of TFT. The mixture was diluted with DCM, and thenstirred for 5 min. The reaction was analyzed by19F NMR, and thenwashed 3 with 1 N NaOH (aq.). The combined aqueous layer wasextracted 2 with DCM, and the combined organic layers weredried over Na2SO4 and concentrated in vacuo. The residue wasloaded onto celite and then puried by ash reverse phase chro-matography with gradient elution from 98% H2O in MeCN to 100%MeCN to provide the desired product in >95% purity.
  • 44
  • [ 124-38-9 ]
  • [ 84750-93-6 ]
  • [ 110915-30-5 ]
YieldReaction ConditionsOperation in experiment
70% Stage #1: carbon dioxide; 1,1-difluoro-2-(4-bromophenyl)ethene With copper(I) thiophene-2-carboxylate; 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene; bis(pinacol)diborane; lithium tert-butoxide In N,N-dimethyl-formamide at 80℃; for 24h; Stage #2: With hydrogenchloride In water stereoselective reaction;
  • 45
  • [ 13120-33-7 ]
  • [ 84750-93-6 ]
  • 4-(4-bromophenyl)-3,3-difluoro-1-methyl-3,4-dihydroquinolin-2(1H)-one [ No CAS ]
YieldReaction ConditionsOperation in experiment
54% With potassium 1,2-ethanedisulfonate; silver nitrate In water; acetone at 50℃; for 9h; Inert atmosphere; Schlenk technique;
  • 46
  • [ 1211417-77-4 ]
  • [ 84750-93-6 ]
  • (2-(4-bromophenyl)-1,1-difluoroethyl)(1,3-dimethyl-1H-imidazol-3-ium-2-yl)dihydroborate [ No CAS ]
YieldReaction ConditionsOperation in experiment
58% With 2,2'-azobis(isobutyronitrile) In toluene at 80℃; Schlenk technique; Sealed tube; Inert atmosphere;
  • 47
  • [ 873-75-6 ]
  • 2,2‐difluoro‐2‐(triphenylphosphonio)acetate [ No CAS ]
  • [ 84750-93-6 ]
YieldReaction ConditionsOperation in experiment
76% With Burgess Reagent; dimethyl sulfoxide at 40℃; for 20h; Inert atmosphere; Sealed tube; General procedure for the one-step process General procedure: Into a 10 mL sealed tube were added alcohol 1 (0.8 mmol), Ph3P+CF2CO2- (855.2 mg, 2.4 mmol), Burgess reagent (1.04 mmol) and anhydrous DMSO (4 mL) under a N2 atmosphere. The tube was sealed and the resulting mixture was stirred at 40 °C for 20 h. After being cooled to room temperature, the mixture was filtered through a plug of Celite, and the solid was washed with DCM. The combined organic phase was washed with brine (10 mL × 3) and water (10 mL × 3) and dried with Na2SO4. The solvent was removed by concentration under vacuum, and the residue was subjected to flash column chromatography to give the final product.
  • 48
  • [ 84750-93-6 ]
  • [ 91-60-1 ]
  • 1-(4-bromophenyl)-2,2-difluoro-2-(naphthalen-2-ylthio)ethan-1-one [ No CAS ]
YieldReaction ConditionsOperation in experiment
80% With oxygen In tetrahydrofuran at 35℃; for 12h; Schlenk technique; Sealed tube;
80% With oxygen In tetrahydrofuran at 35℃; for 12h; 8 in an oxygen atmosphere, in a reaction flask containing 25 ml, add 0.2 mmol 4-(2,2-difluorovinyl)bromobenzene, 0.4 mmol 2-naphthalenethiol and 2 ml tetrahydrofuran , the reaction system was stirred at 35 ° C for 12 hours, the heating and stirring were stopped, water and ethyl acetate were added to extract the reaction solution, the ethyl acetate layer was subjected to reduced pressure rotary evaporation, the solvent was removed, and then the target was separated and purified by column chromatography. product, the column chromatography eluent used is petroleum ether:ethyl acetate=100:1 (volume ratio); the yield of the product is 80%.
  • 49
  • Li[(phenyl)(butyl)B((pinacol)(-2H))] [ No CAS ]
  • [ 84750-93-6 ]
  • (Z)-1-bromo-4-(2-fluoro-2-phenylvinyl)benzene [ No CAS ]
YieldReaction ConditionsOperation in experiment
63% With nickel(II) bromide dimethoxyethane; 4,4'-dimethyl-2,2'-bipyridines; zinc dibromide In tetrahydrofuran; diethyl ether at 0℃; for 12h; Inert atmosphere; Schlenk technique; stereoselective reaction; General Procedure for nickel-catalyzed difluorinative coupling of gem-difluoroalkenes General procedure: 4,4’-Dimethyl-2,2’-dipyridyl (1.4 mg, 0.0075 mmol) was placed into an oven-driedSchlenk tube that was equipped with a stirring bar in a glove box under an argonatmosphere. NiBr2•DME (4.7 mg, 0.015 mmol), ZnBr2 (22.0 mg, 0.150 mmol),lithium organoborates (0.38 g, 0.90 mmol), Et2O:THF (v:v = 9:1, 3.0 mL) were added.The mixture was stirred at 0 oC. The tube was taken out from the glovebox and underan argon atmosphere, gem-difluoroalkenes substrate (0.3 mmol) was added. Themixture was further stirred at 0 oC for 12 h. The mixture was concentrated in vacuoand the residue was purified by flash chromatography on silica gel.
  • 50
  • [ 4381-25-3 ]
  • [ 84750-93-6 ]
  • 2-(4-bromophenyl)-N-[methyl(oxo)(phenyl)-λ6-sulfaneylidene]-2-oxoacetamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
49% With N-Bromosuccinimide In dichloromethane at 20℃; for 18h; Sealed tube; Irradiation;
  • 51
  • [ 84750-93-6 ]
  • [ 16532-79-9 ]
YieldReaction ConditionsOperation in experiment
86% With ammonium hydroxide In acetonitrile at 60℃; for 24h; Sealed tube; Green chemistry;
  • 52
  • [ 66646-88-6 ]
  • [ 84750-93-6 ]
  • C18H16BrF2NO2 [ No CAS ]
YieldReaction ConditionsOperation in experiment
85% With (S)-(+)-5,5’-bis[di(3,5-di-tert-butyl-4-methoxyphenyl)phosphino]-4,4’-bi-1,3-benzodioxole; tetrakis(actonitrile)copper(I) hexafluorophosphate; potassium <i>tert</i>-butylate at 80℃; for 48h; Inert atmosphere; stereoselective reaction;
  • 53
  • [ 76862-09-4 ]
  • [ 84750-93-6 ]
  • C18H15BrClF2NO2 [ No CAS ]
YieldReaction ConditionsOperation in experiment
79% With (S)-(+)-5,5’-bis[di(3,5-di-tert-butyl-4-methoxyphenyl)phosphino]-4,4’-bi-1,3-benzodioxole; tetrakis(actonitrile)copper(I) hexafluorophosphate; potassium <i>tert</i>-butylate at 80℃; for 48h; Inert atmosphere; stereoselective reaction;
  • 54
  • [ 84750-93-6 ]
  • [ 84379-72-6 ]
  • (Z)-1-bromo-4-(2-fluoro-3,3-dimethylbut-1-en-1-yl)benzene [ No CAS ]
YieldReaction ConditionsOperation in experiment
79% With [Ru(bpy)3]Cl2*6H2O; Sodium hydrogenocarbonate; di-tert-butyl 1,4-dihydro-2,6-dimethyl-3,5-pyridine-dicarboxylate In dimethyl sulfoxide at 20℃; for 24h; Inert atmosphere; Irradiation;
Same Skeleton Products
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