Fluorinating reagent
A rapid growth of interest in fluoro-organics has occurred in many areas of application, including polymers and materials, specialtysolvents, performance fluids, medicinal agents, agrochemicalsand in numerous reagents and intermediates for chemical synthesis. However, most of these fluorinating agents are highly aggressive, unstable, and require special equipment and care for safe handling. Shanghai IS Chemical is pleased to offer the following alternatives, which lack these drawbacks.
I05-0051

DAST
38078-09-0
I14-3367

BAST
202289-38-1
I14-2954

Selectfluor fluorinating reagent
140681-55-6
I02-1744

Olah’s reagent
32001-55-1
I14-10188

Morph-DAST
51010-74-3
I01-0259

NFSI
133745-75-2
I14-6179

Triethylamine trihydrofluoride
73602-61-6
I14-0167

Ruppert’s Reagent
81290-20-2
I14-0264

TBAF
429-41-4
I14-1745

Ishikawa reagent
309-88-6
I05-0051

DAST
38078-09-0
The application of DAST.
DAST has proven itself to be an extremely popular reagent for nucleophilic fluorination, due to its ease of handling and versatility. It has regularly been employed in a myriad selective fluorinations of alcohols, alkenols, carbohydrates, ketones, sulfides, epoxides, thioethers, and cyanohydrins.
A solution of 1.18 g (0.01 mol) of compound 1 in 2.0 mL of methylene chloride was slowly added to a solution of 1.25 g (0.01 mol) of DAST in 5.0 mL of methylene chloride cooled to -78 oC. The reaction mixture was warmed to room temperature and mixed with cold water. The lower layer was separated, washed with water, dried (MgS04), and distilled to give 0.93 g of compound 2 as a colorless liquid.
The application of BAST
BAST-Bis(2-methoxyethyl)aminosulfur trifluoride, (CH3OCH2CH2)2NSF3 (Deoxo-Fluor reagent), is a new deoxofluorinating agent that is much more thermally stable than DAST (C2H5)2NSF3 and its congeners. It is effective for the conversion of alcohols to alkyl fluorides, aldehydes/ketones to the corresponding gem-difluorides, and carboxylic acids to the trifluoromethyl derivatives with, in some cases, superior performance compared to DAST. The enhanced stability is rationalized on the basis of conformational rigidity imposed by a coordination of the alkoxy groups with the electron-deficient sulfur atom of the trifluoride.
The alcohol (10 mmol) in dry CH2Cl2 (3.0 mL) was added at the temperature indicated in Table 1, under N2, to a solution of the Phenyl-methanol 1 (2.43 g, 11 mmol) in CH2Cl2 (2.0 mL) in a 50 mL, three-neck flask equipped with a N2 inlet tube, septum, and a magnetic stirring bar. The reaction was monitored by GC/MS for disappearance of the starting material. On completion, the mixture was poured into saturated NaHCO3 (25 mL), and after CO2 evolution ceased it was extracted into CH2Cl2 (3X15 mL), dried (Na2SO4), filtered, and evaporated in vacuo. Flash chromatography on silica gel in hexane/ethyl acetate afforded benzyl fluoride17 (2, 1.05 g, 96%).
The application of selectfluor fluorinating reagent.
To a suspension of NaH ( 1.17 g, 48.8 mmol, 1.2 equiv) in THF (21 mL) was added diethyl 2-(2-(benzyloxy)ethyl)malonate (11.98 g, 40.7 mmol, 1.0 equiv.). The reaction mixture was stirred at 70 °C for 12 h. The solution was cooled to room temperature and diluted with THF (210 mL) and DMF (210 mL), cooled to 0 °C and selectfluor® was added (15.4 g, 43.4 mmol, 1.1 equiv). The solution was stirred for 4 h at 0 °C and warmed to room temperature. The reaction mixture was quenched by the addition of H2O and extracted with Et2O. The organic layers were dried over MgSO4, filtered and concentrated. The product was obtained as a colorless oil after purification via column chromatography (CH2Cl2) (10.82 g, 85%).
The application of NFSI.
To a solution of NaHMDS (Aldrich, 1.0 M in THF, 2.2 eq.) in dry THF (approximately 0.4 mL NaHMDS/mL THF) at -78 °C was added a solution of the benzylic phosphonates (1.0 eq.) in dry THF (approximately 15-20 mL THF/mmol phosphonate) over a period of 2 minutes. The resulting orange to dark red solution (sometimes a suspension forms) was stirred for 1 h at -78 °C. A solution of NFBS (Aldrich, 2.5 eq.) in dry THF (approximately 2-4 mL THF/mmol NFBS) was added over a period of two minutes, during which time the solution (suspension becomes a solution) turned from dark red or orange to yellow-brown. After addition, the solution was stirred for 1-2 hours and then allowed to warm to -30 °C during which time a precipitate formed. The reaction was quenched with 0.01 N HC1 and the resulting solution (precipitate dissolves) was extracted with EtOAc. The organics were combined and washed with 5 % NaHCO3, brine, dried (MgSO4) and concentrated by rotary evaporation to give a yellow oil, which was purified via flash chromatography, 79 % yield.
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