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Chemical Structure| 70395-35-6 Chemical Structure| 70395-35-6

Structure of Sodium chlorofluoroacetate
CAS No.: 70395-35-6

Chemical Structure| 70395-35-6

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Product Details of [ 70395-35-6 ]

CAS No. :70395-35-6
Formula : C2HClFNaO2
M.W : 134.47
SMILES Code : O=C([O-])C(Cl)F.[Na+]
MDL No. :MFCD01861160
Boiling Point : No data available
InChI Key :CETNZZYKKVKEFX-UHFFFAOYSA-M
Pubchem ID :2782421

Safety of [ 70395-35-6 ]

GHS Pictogram:
Signal Word:Warning
Hazard Statements:H302-H315-H319-H335
Precautionary Statements:P261-P264-P270-P271-P280-P301+P312-P302+P352-P304+P340-P305+P351+P338-P330-P332+P313-P337+P313-P362-P403+P233-P405-P501

Application In Synthesis of [ 70395-35-6 ]

* 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 [ 70395-35-6 ]

[ 70395-35-6 ] Synthesis Path-Downstream   1~35

  • 1
  • [ 96290-79-8 ]
  • [ 70395-35-6 ]
YieldReaction ConditionsOperation in experiment
504 g (94%) With sodium hydroxide; A. Sodium Chlorofluoroacetate STR24 Eight hundred ml (4 mole) of 5 N sodium hydroxide was added dropwise over a period of 30 min. to a stirred sample of 523.8 g (4.0 mole) of ethyl chlorofluoroacetate (prepared as described by B. Englund, "Organic Syntheses," Col. Vol. IV, p. 184, John Wiley and Sons, Inc., New York, 1963) contained in a 1-liter flask cooled in an ice bath. Stirring was continued until a homogenous solution was obtained (about 30 min.), and then the resulting solution was evaporated to dryness at 100 and under reduced pressure. The white residue was broken up and dried in a vacuum oven at 80 to give 504 g (94%) of sodium chlorofluoroacetate as a white crystalline powder.
504 g (94%) With sodium hydroxide; Part A. Sodium Chlorofluoroacetate STR11 Eight hundred ml (4 mole) of 5N sodium hydroxide was added dropwise over a period of 30 min. to a stirred sample of 523.8 g (4.0 mole) of ethyl chlorofluoroacetate (prepared as described by B. Englund, "Organic Syntheses," Col. Vol. IV, p. 184, John Wiley and Sons, Inc., New York, 1963) contained in a 1-liter flask cooled in an ice bath. Stirring was continued until a homogenous solution was obtained (about 30 min.), and then the resulting solution was evaporated to dryness at 100 and under reduced pressure. The white residue was broken up and dried in a vacuum oven at 80 to give 504 g (94%) of sodium chlorofluoroacetate as a white crystalline powder.
  • 2
  • [ 70395-35-6 ]
  • [ 359-32-0 ]
YieldReaction ConditionsOperation in experiment
Part B. Chlorofluoroacetyl Chloride STR25 A 3-l., three-necked flask was fitted with a thermometer, a heating mantle, a mechanical stirrer, and a distillation head with a condenser and a 500 ml receiving flask backed up by a dry ice cooled trap. The reaction flask was charged with 500 g (3.72 mole) of crude <strong>[70395-35-6]sodium chlorofluoroacetate</strong> and 1 l. (1400 g. 6.9 mole) of practical grade phthaloyl chloride. The stirrer was started, and the contents of the flask were heated slowly until product began to distill from the reaction mixture (pot temperature about 100-110). The heating mantle was turned off until the initial reaction subsided, and then heating was resumed and continued until the pot temperature reached 245. The distillate in the receiver and the dry ice cooled trap were combined (437 g. 90% crude yield) and redistilled through an 18 in. spinning band column to give 330.8 g (68%) of chlorofluoroacetyl chloride as a colorless liquid, bp 69-69.5. The fraction boiling between 65 and 69 was redistilled to give an additional 45.3 g (9.3%), which is a total yield of 376.1 g (77%) of product boiling at 69-69.5.
Part B. Chlorofluoroacetyl Chloride STR12 A 3-l., three-necked flask was fitted with a thermometer, a heating mantle, a mechanical stirrer, and a distillation head with a condenser and a 500 ml receiving flask backed up by a dry ice cooled trap. The reaction flask was charged with 500 g (3.72 mole) of crude <strong>[70395-35-6]sodium chlorofluoroacetate</strong> and 1 l. (1400 g, 6.9 mole) of practical grade phthaloyl chloride. The stirrer was started, and the contents of the flask were heated slowly until product began to distill from the reaction mixture (pot temperature about 100-110). The heating mantle was turned off until the initial reaction subsided, and then heating was resumed and continued until the pot temperature reached 245. The distillate in the receiver and the dry ice cooled trap were combined (437 g, 90% crude yield) and redistilled through an 18 in. spinning band column to give 330.8 g (68%) of chlorofluoroacetyl chloride as a colorless liquid, bp 69-69.5. The fraction boiling between 65 and 69 was redistilled to give an additional 45.3 g (9.3%), which is a total yield of 376.1 g (77%) of product boiling at 69-69.5.
  • 3
  • [ 58101-60-3 ]
  • [ 70395-35-6 ]
  • [ 1093750-99-2 ]
YieldReaction ConditionsOperation in experiment
In diethylene glycol dimethyl ether; at 160℃; 1. methyl 6,6-difluorobicyclo[3.1.0]hexane-3-carboxylate This compound is prepared following a procedure similar to that used by Nelson,/. Med. Chem. (1990) 3.3:833-38. A solution of methyl 3-cyclopentenecarboxylate in diglyme is heated to 16O0C in an oil bath and stirred vigorously. Eight molar equivalents of sodium chlorofluoro acetate are added and the mixture heated for 1 h. An additional quantity (8 equivalents) of the reagent is added and heated for 30 min before cooling.The reaction mixture is partitioned between water and ethyl acetate and the organic layer is dried (Na2SO4) and concentrated under reduced pressure. Flash chromatography on silica gel yields the geminal-difluoro compound.
  • 4
  • (S)-N-(5-[4-(1H-indol-3-yl)-5-(trifluoromethyl)pyrimidin-2-yl]amino}-2-({2-[but-3-yn-1-yl-(methyl)amino]ethyl}(methyl)amino)-4-methoxyphenyl)-2-aminopropanamide [ No CAS ]
  • [ 70395-35-6 ]
  • C33H35ClF4N8O3 [ No CAS ]
  • 5
  • C26H31ClN8O2 [ No CAS ]
  • [ 70395-35-6 ]
  • 2-chloro-N-(2-((5-((5-chloro-4-(1H-indol-3-yl)pyrimidin-2-yl)amino)-2-((2-(dimethylamino)-ethyl)(methyl)amino)-4-methoxyphenyl)amino)-2-oxoethyl)-2-fluoroacetamide [ No CAS ]
  • 6
  • C30H39ClN8O2 [ No CAS ]
  • [ 70395-35-6 ]
  • (2S)-2-(2-chloro-2-fluoroacetamido)-N-(5-((5-chloro-4-(1H-indol-3-yl)pyrimidin-2-yl)amino)-2-((2-(dimethylamino)ethyl)(methyl)amino)-4-methoxyphenyl)-4-methylpentanamide [ No CAS ]
  • 7
  • C27H33ClN8O3 [ No CAS ]
  • [ 70395-35-6 ]
  • (2S)-2-(2-chloro-2-fluoroacetamido)-N-(5-((5-chloro-4-(1H-indol-3-yl)pyrimidin-2-yl)amino)-2-((2-(dimethylamino)ethyl)(methyl)amino)-4-methoxyphenyl)-3-hydroxypropanamide [ No CAS ]
  • 8
  • C29H35ClN8O2 [ No CAS ]
  • [ 70395-35-6 ]
  • (2S)-1-(2-chloro-2-fluoroacetyl)-N-(5-((5-chloro-4-(1H-indol-3-yl)pyrimidin-2-yl)amino)-2-((2-(dimethylamino)ethyl)(methyl)amino)-4-methoxyphenyl)pyrrolidine-2-carboxamide [ No CAS ]
  • 9
  • C29H35ClN8O3 [ No CAS ]
  • [ 70395-35-6 ]
  • (2S,4R)-1-(2-chloro-2-fluoroacetyl)-N-(5-((5-chloro-4-(1H-indol-3-yl)pyrimidin-2-yl)amino)-2-((2-(dimethylamino)ethyl)(methyl)amino)-4-methoxyphenyl)-4-hydroxypyrrolidine-2-carboxamide [ No CAS ]
  • 10
  • C28H33ClN8O2 [ No CAS ]
  • [ 70395-35-6 ]
  • (2S)-1-(2-chloro-2-fluoroacetyl)-N-(5-((5-chloro-4-(1H-indol-3-yl)pyrimidin-2-yl)amino)-2-((2-(dimethylamino)ethyl)(methyl)amino)-4-methoxyphenyl)azetidine-2-carboxamide [ No CAS ]
  • 11
  • C27H33ClN8O2 [ No CAS ]
  • [ 70395-35-6 ]
  • (2S)-2-(2-chloro-2-fluoroacetamido)-N-(5-((5-chloro-4-(1H-indol-3-yl)pyrimidin-2-yl)-amino)-2-((2-(dimethylamino)ethyl)(methyl)amino)-4-methoxyphenyl)propanamide [ No CAS ]
  • 12
  • C27H33ClN8O2 [ No CAS ]
  • [ 70395-35-6 ]
  • (2R)-2-(2-chloro-2-fluoroacetamido)-N-(5-((5-chloro-4-(1H-indol-3-yl)pyrimidin-2-yl)-amino)-2-((2-(dimethylamino)ethyl)(methyl)amino)-4-methoxyphenyl)propanamide [ No CAS ]
  • 13
  • N4-[4-(1H-indol-3-yl)-5-(trifluoromethyl)pyrimidin-2-yl]-N1-[2-(dimethylamino)ethyl]-5-methoxy-N1-methylbenzene-1,2,4-triamine [ No CAS ]
  • [ 70395-35-6 ]
  • N-(5-((4-(1H-indol-3-yl)-5-(trifluoromethyl)pyrimidin-2-yl)amino)-2-((2-(dimethylamino)ethyl)-(methyl)amino)-4-methoxyphenyl)-2-chloro-2-fluoroacetamide [ No CAS ]
  • 14
  • C27H34N8O2 [ No CAS ]
  • [ 70395-35-6 ]
  • (2S)-N-(5-((4-(1H-indol-3-yl)pyrimidin-2-yl)amino)-2-((2-(dimethylamino)ethyl)(methyl)amino)-4-methoxyphenyl)-2-(2-chloro-2-fluoroacetamido)propanamide [ No CAS ]
  • 15
  • C27H33FN8O2 [ No CAS ]
  • [ 70395-35-6 ]
  • (2S)-2-(2-chloro-2-fluoroacetamido)-N-(2-((2-(dimethylamino)ethyl)(methyl)amino)-5-((5-fluoro-4-(1H-indol-3-yl)pyrimidin-2-yl)amino)-4-methoxyphenyl)propanamide [ No CAS ]
  • 16
  • C28H36N8O2 [ No CAS ]
  • [ 70395-35-6 ]
  • (2S)-N-(5-((4-(1H-Indol-3-yl)-5-methylpyrimidin-2-yl)amino)-2-((2-(dimethylamino)ethyl)-(methyl)amino)-4-methoxyphenyl)-2-(2-chloro-2-fluoroacetamido)propanamide [ No CAS ]
  • 17
  • C29H34N8O2 [ No CAS ]
  • [ 70395-35-6 ]
  • (2S)-2-(2-chloro-2-fluoroacetamido)-N-(2-((2-(dimethylamino)ethyl)(methyl)amino)-5-((5-ethynyl-4-(1H-indol-3-yl)pyrimidin-2-yl)amino)-4-methoxyphenyl)propanamide [ No CAS ]
  • 18
  • C28H33N9O2 [ No CAS ]
  • [ 70395-35-6 ]
  • (2S)-2-(2-chloro-2-fluoroacetamido)-N-(5-((5-cyano-4-(1H-indol-3-yl)pyrimidin-2-yl)amino)-2-((2-(dimethylamino)ethyl)(methyl)amino)-4-methoxyphenyl)propanamide [ No CAS ]
  • 19
  • C28H36N8O3 [ No CAS ]
  • [ 70395-35-6 ]
  • (2S)-N-(5-((4-(1H-indol-3-yl)-5-methoxypyrimidin-2-yl)amino)-2-((2-(dimethylamino)ethyl)-(methyl)amino)-4-methoxyphenyl)-2-(2-chloro-2-fluoroacetamido)propanamide [ No CAS ]
  • 20
  • C27H33BrN8O2 [ No CAS ]
  • [ 70395-35-6 ]
  • (2S)-N-(5-((5-bromo-4-(1H-indol-3-yl)pyrimidin-2-yl)amino)-2-((2-(dimethylamino)ethyl)-(methyl)amino)-4-methoxyphenyl)-2-(2-chloro-2-fluoroacetamido)propanamide [ No CAS ]
  • 21
  • C28H33F3N8O2 [ No CAS ]
  • [ 70395-35-6 ]
  • (2S)-N-(5-((4-(1H-indol-3-yl)-5-(trifluoromethyl)pyrimidin-2-yl)amino)-2-((2-(dimethylamino)-ethyl)(methyl)amino)-4-methoxyphenyl)-2-(2-chloro-2-fluoroacetamido)propanamide [ No CAS ]
  • 22
  • [ 1421372-61-3 ]
  • [ 70395-35-6 ]
  • 2-chloro-N-(5-((5-chloro-4-(1H-indol-3-yl)pyrimidin-2-yl)amino)-2-((2-(dimethylamino)-ethyl)(methyl)amino)-4-methoxyphenyl)-2-fluoroacetamide [ No CAS ]
  • 23
  • 2-(2-((tert-butyldimethylsilyl)oxy)ethyl)-N-methylaniline [ No CAS ]
  • [ 70395-35-6 ]
  • C17H27ClFNO2Si [ No CAS ]
  • 24
  • 4-{2-[2-(prop-2-yn-1-yloxy)ethoxy]ethoxy}aniline [ No CAS ]
  • [ 70395-35-6 ]
  • 2-chloro-2-fluoro-N-(4-{2-[2-(prop-2-yn-1-yloxy)ethoxy]ethoxy}phenyl)acetamide [ No CAS ]
  • 25
  • [ 82261-42-5 ]
  • [ 70395-35-6 ]
  • 2-chloro-2-fluoro-N-[4-(pyridin-3-yl)phenyl]acetamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
94% With 2,4,6-tripropyl-1,3,5,2,4,6-trioxatriphosphinane-2,4,6-trioxide; N-ethyl-N,N-diisopropylamine; In dichloromethane; ethyl acetate; at 0 - 20℃; for 1.0h; General procedure: To a stirred solution of 5-amino-1-naphthol (126 mg, 0.792 mmol) and <strong>[70395-35-6]sodium chlorofluoroacetate</strong> (159 mg,1.18 mmol) in dichloromethane (8 mL) was added T3P (50 wt%solution in AcOEt, 701 μL, 1.18 mmol) and N,N-diisopropylethylamine(DIPEA) (273 μL, 1.57 mmol) at 0C. Afterstirred at ambient temperature for 1 h, the reaction mixturewas diluted with water and extracted thrice with CHCl3. Thecombined organic layers were washed with brine, dried overNa2SO4, filtered and concentrated in vacuo. The residue waspurified by flash column chromatography on silica gel (hexane/AcOEt = 3 : 1) to afford the title compound (37.2 mg, 18% yield) as a pale purple solid.
  • 26
  • [ 40034-44-4 ]
  • [ 70395-35-6 ]
  • 2-chloro-2-fluoro-N-[3-(pyridin-4-yl)phenyl]acetamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
79% With 2,4,6-tripropyl-1,3,5,2,4,6-trioxatriphosphinane-2,4,6-trioxide; N-ethyl-N,N-diisopropylamine; In dichloromethane; ethyl acetate; at 0 - 20℃; for 1.0h; General procedure: To a stirred solution of 5-amino-1-naphthol (126 mg, 0.792 mmol) and <strong>[70395-35-6]sodium chlorofluoroacetate</strong> (159 mg,1.18 mmol) in dichloromethane (8 mL) was added T3P (50 wt%solution in AcOEt, 701 μL, 1.18 mmol) and N,N-diisopropylethylamine(DIPEA) (273 μL, 1.57 mmol) at 0C. Afterstirred at ambient temperature for 1 h, the reaction mixturewas diluted with water and extracted thrice with CHCl3. Thecombined organic layers were washed with brine, dried overNa2SO4, filtered and concentrated in vacuo. The residue waspurified by flash column chromatography on silica gel (hexane/AcOEt = 3 : 1) to afford the title compound (37.2 mg, 18% yield) as a pale purple solid.
  • 27
  • [ 57976-57-5 ]
  • [ 70395-35-6 ]
  • 2-chloro-2-fluoro-N-[3-(pyridin-3-yl)phenyl]acetamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
41% With 2,4,6-tripropyl-1,3,5,2,4,6-trioxatriphosphinane-2,4,6-trioxide; N-ethyl-N,N-diisopropylamine; In dichloromethane; ethyl acetate; at 0 - 20℃; for 1.0h; General procedure: To a stirred solution of 5-amino-1-naphthol (126 mg, 0.792 mmol) and <strong>[70395-35-6]sodium chlorofluoroacetate</strong> (159 mg,1.18 mmol) in dichloromethane (8 mL) was added T3P (50 wt%solution in AcOEt, 701 μL, 1.18 mmol) and N,N-diisopropylethylamine(DIPEA) (273 μL, 1.57 mmol) at 0C. Afterstirred at ambient temperature for 1 h, the reaction mixturewas diluted with water and extracted thrice with CHCl3. Thecombined organic layers were washed with brine, dried overNa2SO4, filtered and concentrated in vacuo. The residue waspurified by flash column chromatography on silica gel (hexane/AcOEt = 3 : 1) to afford the title compound (37.2 mg, 18% yield) as a pale purple solid.
  • 28
  • [ 580-15-4 ]
  • [ 70395-35-6 ]
  • 2-chloro-2-fluoro-N-(quinolin-6-yl)acetamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
76% With 2,4,6-tripropyl-1,3,5,2,4,6-trioxatriphosphinane-2,4,6-trioxide; N-ethyl-N,N-diisopropylamine; In dichloromethane; ethyl acetate; at 0 - 20℃; for 1h; General procedure: To a stirred solution of 5-amino-1-naphthol (126 mg, 0.792 mmol) and sodium chlorofluoroacetate (159 mg,1.18 mmol) in dichloromethane (8 mL) was added T3P (50 wt%solution in AcOEt, 701 μL, 1.18 mmol) and N,N-diisopropylethylamine(DIPEA) (273 μL, 1.57 mmol) at 0C. Afterstirred at ambient temperature for 1 h, the reaction mixturewas diluted with water and extracted thrice with CHCl3. Thecombined organic layers were washed with brine, dried overNa2SO4, filtered and concentrated in vacuo. The residue waspurified by flash column chromatography on silica gel (hexane/AcOEt = 3 : 1) to afford the title compound (37.2 mg, 18% yield) as a pale purple solid.
  • 29
  • [ 578-66-5 ]
  • [ 70395-35-6 ]
  • 2-chloro-2-fluoro-N-(quinolin-8-yl)acetamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
75% With 2,4,6-tripropyl-1,3,5,2,4,6-trioxatriphosphinane-2,4,6-trioxide; N-ethyl-N,N-diisopropylamine; In dichloromethane; ethyl acetate; at 0 - 20℃; for 3.0h; General procedure: To a stirred solution of 5-amino-1-naphthol (126 mg, 0.792 mmol) and <strong>[70395-35-6]sodium chlorofluoroacetate</strong> (159 mg,1.18 mmol) in dichloromethane (8 mL) was added T3P (50 wt%solution in AcOEt, 701 μL, 1.18 mmol) and N,N-diisopropylethylamine(DIPEA) (273 μL, 1.57 mmol) at 0C. Afterstirred at ambient temperature for 1 h, the reaction mixturewas diluted with water and extracted thrice with CHCl3. Thecombined organic layers were washed with brine, dried overNa2SO4, filtered and concentrated in vacuo. The residue waspurified by flash column chromatography on silica gel (hexane/AcOEt = 3 : 1) to afford the title compound (37.2 mg, 18% yield) as a pale purple solid.
  • 30
  • [ 611-34-7 ]
  • [ 70395-35-6 ]
  • 2-chloro-2-fluoro-N-(quinolin-5-yl)acetamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
91% With 2,4,6-tripropyl-1,3,5,2,4,6-trioxatriphosphinane-2,4,6-trioxide; N-ethyl-N,N-diisopropylamine; In dichloromethane; ethyl acetate; at 0 - 20℃; for 1.0h; General procedure: To a stirred solution of 5-amino-1-naphthol (126 mg, 0.792 mmol) and <strong>[70395-35-6]sodium chlorofluoroacetate</strong> (159 mg,1.18 mmol) in dichloromethane (8 mL) was added T3P (50 wt%solution in AcOEt, 701 μL, 1.18 mmol) and N,N-diisopropylethylamine(DIPEA) (273 μL, 1.57 mmol) at 0C. Afterstirred at ambient temperature for 1 h, the reaction mixturewas diluted with water and extracted thrice with CHCl3. Thecombined organic layers were washed with brine, dried overNa2SO4, filtered and concentrated in vacuo. The residue waspurified by flash column chromatography on silica gel (hexane/AcOEt = 3 : 1) to afford the title compound (37.2 mg, 18% yield) as a pale purple solid.
  • 31
  • [ 580-17-6 ]
  • [ 70395-35-6 ]
  • 2-chloro-2-fluoro-N-(quinolin-3-yl)acetamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
77% With 2,4,6-tripropyl-1,3,5,2,4,6-trioxatriphosphinane-2,4,6-trioxide; N-ethyl-N,N-diisopropylamine; In dichloromethane; ethyl acetate; at 0 - 20℃; for 1.5h; General procedure: To a stirred solution of 5-amino-1-naphthol (126 mg, 0.792 mmol) and <strong>[70395-35-6]sodium chlorofluoroacetate</strong> (159 mg,1.18 mmol) in dichloromethane (8 mL) was added T3P (50 wt%solution in AcOEt, 701 μL, 1.18 mmol) and N,N-diisopropylethylamine(DIPEA) (273 μL, 1.57 mmol) at 0C. Afterstirred at ambient temperature for 1 h, the reaction mixturewas diluted with water and extracted thrice with CHCl3. Thecombined organic layers were washed with brine, dried overNa2SO4, filtered and concentrated in vacuo. The residue waspurified by flash column chromatography on silica gel (hexane/AcOEt = 3 : 1) to afford the title compound (37.2 mg, 18% yield) as a pale purple solid.
  • 32
  • [ 70395-35-6 ]
  • [ 3977-29-5 ]
  • 2-chloro-2-fluoro-N-(4-hydroxy-6-methylpyrimidin-2-yl)acetamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
19% With 2,4,6-tripropyl-1,3,5,2,4,6-trioxatriphosphinane-2,4,6-trioxide; N-ethyl-N,N-diisopropylamine; In dichloromethane; ethyl acetate; at 0 - 20℃; for 4.0h; General procedure: To a stirred solution of 5-amino-1-naphthol (126 mg, 0.792 mmol) and <strong>[70395-35-6]sodium chlorofluoroacetate</strong> (159 mg,1.18 mmol) in dichloromethane (8 mL) was added T3P (50 wt%solution in AcOEt, 701 μL, 1.18 mmol) and N,N-diisopropylethylamine(DIPEA) (273 μL, 1.57 mmol) at 0C. Afterstirred at ambient temperature for 1 h, the reaction mixturewas diluted with water and extracted thrice with CHCl3. Thecombined organic layers were washed with brine, dried overNa2SO4, filtered and concentrated in vacuo. The residue waspurified by flash column chromatography on silica gel (hexane/AcOEt = 3 : 1) to afford the title compound (37.2 mg, 18% yield) as a pale purple solid.
  • 33
  • [ 70395-35-6 ]
  • [ 1749-71-9 ]
  • 2-chloro-2-fluoro-N-(5-methoxy-4-methylpyrimidin-2-yl)acetamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
48% With 2,4,6-tripropyl-1,3,5,2,4,6-trioxatriphosphinane-2,4,6-trioxide; N-ethyl-N,N-diisopropylamine; In dichloromethane; ethyl acetate; at 0 - 20℃; for 3.0h; General procedure: To a stirred solution of 5-amino-1-naphthol (126 mg, 0.792 mmol) and <strong>[70395-35-6]sodium chlorofluoroacetate</strong> (159 mg,1.18 mmol) in dichloromethane (8 mL) was added T3P (50 wt%solution in AcOEt, 701 μL, 1.18 mmol) and N,N-diisopropylethylamine(DIPEA) (273 μL, 1.57 mmol) at 0C. Afterstirred at ambient temperature for 1 h, the reaction mixturewas diluted with water and extracted thrice with CHCl3. Thecombined organic layers were washed with brine, dried overNa2SO4, filtered and concentrated in vacuo. The residue waspurified by flash column chromatography on silica gel (hexane/AcOEt = 3 : 1) to afford the title compound (37.2 mg, 18% yield) as a pale purple solid.
  • 34
  • [ 18595-14-7 ]
  • [ 70395-35-6 ]
  • methyl 4-(2-Chloro-2-fluoroacetamido)-3-methylbenzoate [ No CAS ]
YieldReaction ConditionsOperation in experiment
78% With 2,4,6-tripropyl-1,3,5,2,4,6-trioxatriphosphinane-2,4,6-trioxide; N-ethyl-N,N-diisopropylamine; In dichloromethane; ethyl acetate; at 0 - 20℃; for 2.0h; General procedure: To a stirred solution of 5-amino-1-naphthol (126 mg, 0.792 mmol) and <strong>[70395-35-6]sodium chlorofluoroacetate</strong> (159 mg,1.18 mmol) in dichloromethane (8 mL) was added T3P (50 wt%solution in AcOEt, 701 μL, 1.18 mmol) and N,N-diisopropylethylamine(DIPEA) (273 μL, 1.57 mmol) at 0C. Afterstirred at ambient temperature for 1 h, the reaction mixturewas diluted with water and extracted thrice with CHCl3. Thecombined organic layers were washed with brine, dried overNa2SO4, filtered and concentrated in vacuo. The residue waspurified by flash column chromatography on silica gel (hexane/AcOEt = 3 : 1) to afford the title compound (37.2 mg, 18% yield) as a pale purple solid.
  • 35
  • [ 41748-71-4 ]
  • [ 70395-35-6 ]
  • 2-chloro-2-fluoro-N-(1H-indazol-4-yl)acetamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
22% With 2,4,6-tripropyl-1,3,5,2,4,6-trioxatriphosphinane-2,4,6-trioxide; N-ethyl-N,N-diisopropylamine; In dichloromethane; ethyl acetate; at 0 - 20℃; for 1.5h; General procedure: To a stirred solution of 5-amino-1-naphthol (126 mg, 0.792 mmol) and <strong>[70395-35-6]sodium chlorofluoroacetate</strong> (159 mg,1.18 mmol) in dichloromethane (8 mL) was added T3P (50 wt%solution in AcOEt, 701 μL, 1.18 mmol) and N,N-diisopropylethylamine(DIPEA) (273 μL, 1.57 mmol) at 0C. Afterstirred at ambient temperature for 1 h, the reaction mixturewas diluted with water and extracted thrice with CHCl3. Thecombined organic layers were washed with brine, dried overNa2SO4, filtered and concentrated in vacuo. The residue waspurified by flash column chromatography on silica gel (hexane/AcOEt = 3 : 1) to afford the title compound (37.2 mg, 18% yield) as a pale purple solid.
 

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