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Chemistry
Organic Building Blocks
Aryls
2,2-Difluoropropyl benzoate
Chemistry
Organic Building Blocks
Aryls
Fluorinated Building Blocks Esters

[ CAS No. 784193-14-2 ] {[proInfo.proName]}

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Chemical Structure| 784193-14-2
Chemical Structure| 784193-14-2
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CAS No. :784193-14-2 MDL No. :MFCD22377987
Formula : C10H10F2O2 Boiling Point : -
Linear Structure Formula :- InChI Key :-
M.W : 200.18 Pubchem ID :-
Synonyms :

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Application In Synthesis of [ 784193-14-2 ]

* 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 [ 784193-14-2 ]

[ 784193-14-2 ] Synthesis Path-Downstream   1~2

  • 1
  • [ 784193-14-2 ]
  • [ 33420-52-9 ]
YieldReaction ConditionsOperation in experiment
29% With sodium hydroxide; In diethyl ether; water; at 50℃; for 17h; A two-phase mixture of benzoic acid 2,2-difluoropropyl ester (I-10A-7a; 20 g, 100 mmol) in 1:1.5:2 6N NaOH/H2O/diethyl ether (183 ml) was stirred at 500C for 17 hours. After cooling to ambient temperature, the reaction mixture was extracted with diethyl ether (3*), and the combined extracts were dried and concentrated under reduced pressure. The orange-colored crude residue was distilled to give the desired product, 2,2-difluoropropan-1-ol (I-10A-7b), as a colorless oil (2.8 g, 29%): boiling point-100 C. (1 atm); 1H NMR (400 MHz, CDCl3) delta 3.71 (t, J=12.5 Hz, 2H), 1.64 (t, J=18.7 Hz, 3H).
29% With sodium hydroxide; water; In diethyl ether; at 50℃; for 17h; Preparation of Intermediate 2,2-Difluoropropan-1-ol (I-4A-4b): A two-phase mixture of benzoic acid 2,2-difluoro-propyl ester (I-4A-4a, 20 g, 100 mmol) in 1:1.5:2 6N NaOH/H2O/ether (183 ml) was stirred at 50 C. for 17 h. After cooling to ambient temperature, the reaction mixture was extracted with ether (3*), and the combined extracts were dried and concentrated under reduced pressure. The orange-colored crude residue was distilled to give the desired product, 2,2-difluoro-propan-1-ol (I-4A-4b), as a colorless oil (2.8 g, 29%): boiling point -100 C. (1 atm); 1H NMR (400 MHz, CDCl3): delta 3.71 (t, 2H, J=12.46 Hz), 1.64 (t, 3H, J=18.69 Hz).
With water; sodium hydroxide; In diethyl ether; at 60℃; for 4h; Step 3 (ME-53):A solution of ME-52 (4 g, 20.0 mmol) in diethyl ether (80 mL) was heated at 60C for 4 h.The reaction mass was cooled to room temperature and extracted with diethyl ether. Thecombined organic layer was washed successively with water, brine; dried over anhydroussodium sulfate and concentrated under mild reduced pressure at room temperature to afford4 g of ether containing ME-53.
Reference： [1]Patent: US2004/214837,2004,A1 .Location in patent: Page 33
[2]Patent: US2004/214838,2004,A1 .Location in patent: Page 19
[3]Bioorganic and Medicinal Chemistry Letters,2006,vol. 16,p. 731 - 736
[4]Patent: WO2014/140279,2014,A1 .Location in patent: Page/Page column 69; 125
  • 2
  • [ 6656-60-6 ]
  • [ 784193-14-2 ]
YieldReaction ConditionsOperation in experiment
94% With diethylamino-sulfur trifluoride In ethanol; dichloromethane
4 g With diethylamino-sulfur trifluoride In dichloromethane at 0 - 20℃; for 18h; 14.2 Step 2 (ME-S2) Step 2 (ME-52):Diethylamino sulfurtrifluoride (5.9 mL, 44.94 mmol) was added to a solution of ME-Si (4.0 g,22.47 mmol) in dichloromethane (40 mL) at 0°C and the solution was stirred at roomtemperature for 18 h. The reaction was quenched with ice water and the mixture was extracted with dichloromethane. The combined organic layer was washed successively with water, brine; dried over anhydrous sodium sulfate and concentrated in vacuum to afford 4.Og of ME-52 as a brown liquid.
Reference： [1]Carpino, Philip A.; Griffith, David A.; Sakya, Subas; Dow, Robert L.; Black, Shawn C.; Hadcock, John R.; Iredale, Philip A.; Scott, Dennis O.; Fichtner, Michael W.; Rose, Colin R.; Day, Robert; Dibrino, Joseph; Butler, Mary; DeBartolo, Demetria B.; Dutcher, Darrin; Gautreau, Denise; Lizano, Jeff S.; O'Connor, Rebecca E.; Sands, Michelle A.; Kelly-Sullivan, Dawn; Ward, Karen M. [Bioorganic and Medicinal Chemistry Letters, 2006, vol. 16, # 3, p. 731 - 736]
[2]Current Patent Assignee: VIVORYON THERAPEUTICS AG - WO2014/140279, 2014, A1 Location in patent: Page/Page column 69; 125

Tags: 784193-14-2; 2,2-Difluoropropyl benzoate; Fluorinated Building Blocks

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