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Chemical Structure| 400-92-0 Chemical Structure| 400-92-0

Structure of 400-92-0

Chemical Structure| 400-92-0

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Product Details of [ 400-92-0 ]

CAS No. :400-92-0
Formula : C8H8FNO2
M.W : 169.15
SMILES Code : O=C(N)C1=CC(OC)=CC=C1F
MDL No. :MFCD06409123
Boiling Point : No data available
InChI Key :RJXPZBIQUGIJAB-UHFFFAOYSA-N
Pubchem ID :19028203

Safety of [ 400-92-0 ]

GHS Pictogram:
Signal Word:Warning
Hazard Statements:H302-H315-H319-H335
Precautionary Statements:P261-P280-P301+P312-P302+P352-P305+P351+P338

Application In Synthesis of [ 400-92-0 ]

* 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 [ 400-92-0 ]

[ 400-92-0 ] Synthesis Path-Downstream   1~9

  • 1
  • [ 400-92-0 ]
  • [ 951122-32-0 ]
YieldReaction ConditionsOperation in experiment
82% With boron tribromide; In dichloromethane; at 20.0℃; for 48.0h; (Method H) Boron tribromide solution (1.0 M in CH2CI2, 23.6 ml, 23.6 mmol, 2 equiv.) was added slowly, dropwise to stirred solution of 2-fluoro-5- methoxybenzenecarboxamide (2.0 g, 11.8 mmol, 1 equiv.) in CH2CI2 (60 ml), at r.t., under N2. The reaction mixture was stirred at r.t. for 48 h. The solvent was removed under reduced pressure, the residue was dissolved in water (120 ml) and extracted with EtOAc (4x100 ml). The combined organic extracts were washed with water (2x100 ml), dried (Na2SO4) and filtered through a pad of silica gel. The filtrate was evaporated to dryness under reduced pressure, to give the desired compound as a grey solid (1.5O g, 82%).
YieldReaction ConditionsOperation in experiment
b 2-Fluoro-5-methoxybenzamide In a three-necked round-bottom flask (500 mL), equipped with a magnetic stirrer and a reflux condensor, 2-fluoro-5-methoxybensonic acid (33.8 g; 199 mmol) and thionyl chloride (200 mL) were refluxed under nitrogen for 2 h. The excess of thionyl chloride was evaporated to leave an oily residue which was dissolved in methylene chloride (100 mL) and evaporated. This procedure was repeated three times. The crude acid chloride thus obtained was dissolved in methylene chloride (100 mL) and added dropwise during 10 min to a cold (-40 to -50 C.) and mechanically stirred solution of dry THF (300 mL) and liquid ammonia (100 mL) in a three-necked round-bottom flask (1000 mL) under nitrogen. When the addition was completed the cooling bath was taken away and the mixture was slowly warmed to room temperature while the stirring was continued. Water (50 mL) was added to dissolve the precipitated salt and the two-phase solution obtained was concentrated to dryness by rotary-evaporation. The crude amide was washed repeatedly with small portions of dilute aqueous ammonia followed by water until the washings were colourless. Drying at reduced pressure over night afforded 32.0 g of the title compound as light-brown crystals. Mp. 122-124 C.
  • 3
  • [ 400-92-0 ]
  • [ 62257-15-2 ]
YieldReaction ConditionsOperation in experiment
With sodium hydroxide; bromine; In water; c 2-Fluoro-5-methoxyaniline In a round-bottom flask (500 mL), equipped with a reflux condensor and a magnetic stirrer, bromine (11.4 mL; 223 mmol) was added dropwise to a cold (+4 C.) and stirred solution of sodium hydroxide (35.5 g; 887 mmol) and water (322 mL). Then <strong>[400-92-0]2-fluoro-5-methoxybenzamide</strong> (31.9 g; 189 mmol) was added in portions. The mixture was heated on an oil-bath, refluxed for 1 h, cooled to room temperature and extracted with ether (3*300 mL). Drying the combined ether phases (K2 CO3), filtering, evaporation of the solvent and vacuum distillation of the oily residue afforded 20.1 g of the title compound as a pale yellow oil (bp. 113-114 C./14 mmHg), which solidified in the cold (Mp. 27-28 C.).
  • 4
  • [ 105728-90-3 ]
  • [ 400-92-0 ]
  • 5
  • [ 796120-91-7 ]
  • [ 400-92-0 ]
YieldReaction ConditionsOperation in experiment
General procedure: The aldehydes 10a or 10b (800 mg, 5.2 mmol) were added to a solution of hydroxylamine hydrochloride (725 mg, 10.5 mmol) in DMSO (10 mL), and the reaction mixture was stirred at 100 C for 20 min. The heater was turned off and an aqueous solution of NaOH (600 mg) in H2O (5 mL) was slowly added to the reaction mixture over a 2 min period with stirring, and then 50% hydrogen peroxide (5 mL) was slowly and carefully added over a 10 min period. The reaction mixture was further stirred for 5 min and extracted with ethyl acetate (3 10 mL), dried over anhydrous MgSO4, and evaporated under reduced pressure to afford the corresponding amides 11a and 11b58 as white solids. The crude amides 11a or 11b (1 mmol) and Lawesson’s reagent (490 mg, 1.2 mmol) were added to dry THF (15 mL). The reaction mixture was stirred at room temperature for 3 h. The solvent was evaporated under reduced pressure and the residue was partitioned between aq NaHCO3 (25 mL) and ethyl acetate (25 mL). The organic solvent was separated and dried over anhydrous Na2SO4. The crude product was further purified by silica gel flash chromatography, using hexane-ethyl acetate (4:1), to yield the corresponding thioamides 12a and 12b as yellow solids. The obtained thioamides 12a or 12b (90 mg, 0.5 mmol), 3-methoxy-a-bromoacetophenone 8b (115 mg, 0.5 mmol), and potassium carbonate (175 mg, 0.5 mmol) were added to absolute ethanol (5 mL). The reaction mixture was heated at 70 C for 6 h and then allowed to cool and quenched with distilled water (30 mL). The organic materials were extracted by ethyl acetate (30 mL). The organic layer was isolated and dried over anhydrous Na2SO4. Solvent was evaporated under reduced pressure. The solid residue was purified by silica gel flash chromatography, using hexane-ethyl acetate (9:1, then 4:1), to yield thedesired compounds as solids
  • 6
  • [ 400-92-0 ]
  • [ 1415718-96-5 ]
YieldReaction ConditionsOperation in experiment
With Lawessons reagent; In tetrahydrofuran; at 23.0℃; General procedure: The aldehydes 10a or 10b (800 mg, 5.2 mmol) were added to a solution of hydroxylamine hydrochloride (725 mg, 10.5 mmol) in DMSO (10 mL), and the reaction mixture was stirred at 100 C for 20 min. The heater was turned off and an aqueous solution of NaOH (600 mg) in H2O (5 mL) was slowly added to the reaction mixture over a 2 min period with stirring, and then 50% hydrogen peroxide (5 mL) was slowly and carefully added over a 10 min period. The reaction mixture was further stirred for 5 min and extracted with ethyl acetate (3 10 mL), dried over anhydrous MgSO4, and evaporated under reduced pressure to afford the corresponding amides 11a and 11b58 as white solids. The crude amides 11a or 11b (1 mmol) and Lawesson’s reagent (490 mg, 1.2 mmol) were added to dry THF (15 mL). The reaction mixture was stirred at room temperature for 3 h. The solvent was evaporated under reduced pressure and the residue was partitioned between aq NaHCO3 (25 mL) and ethyl acetate (25 mL). The organic solvent was separated and dried over anhydrous Na2SO4. The crude product was further purified by silica gel flash chromatography, using hexane-ethyl acetate (4:1), to yield the corresponding thioamides 12a and 12b as yellow solids. The obtained thioamides 12a or 12b (90 mg, 0.5 mmol), 3-methoxy-a-bromoacetophenone 8b (115 mg, 0.5 mmol), and potassium carbonate (175 mg, 0.5 mmol) were added to absolute ethanol (5 mL). The reaction mixture was heated at 70 C for 6 h and then allowed to cool and quenched with distilled water (30 mL). The organic materials were extracted by ethyl acetate (30 mL). The organic layer was isolated and dried over anhydrous Na2SO4. Solvent was evaporated under reduced pressure. The solid residue was purified by silica gel flash chromatography, using hexane-ethyl acetate (9:1, then 4:1), to yield thedesired compounds as solids
  • 7
  • [ 127667-01-0 ]
  • [ 400-92-0 ]
YieldReaction ConditionsOperation in experiment
With dihydrogen peroxide; potassium carbonate; In dimethyl sulfoxide; at 20.0℃; for 0.5h; A. 2-Fluoro-5-methoxybenzamide, 36a To a solution of 2-fluoro-5-methoxybenzonitrile (2 g, 13.2 mmol) in DMSO (6.6 mL) was added H2O2 (1.6 mL) and K2CO3 (274 mg, 1.98 mmol). The resulting solution was stirred for 30 min at rt. The reaction was then quenched with NaHCO3 (satd, 30 mL). The resulting solution was extracted with EtOAc (50 mL), and the organic layers were combined, and concentrated under reduced pressure. The residue was purified by flash column chromatography (0-10% EtOAc/petroleum ether) on silica gel to obtain compound 36a as a white solid. 1H-NMR (400 MHz, DMSO-d6) (ppm): 7.66 - 7.70 (m, 2H), 7.04 - 7.23 (m, 3H), 3.77 (s, 3H).
With dihydrogen peroxide; potassium carbonate; In dimethyl sulfoxide; at 20.0℃; for 0.5h; To a solution of 2-fluoro-5-methoxybenzonitrile (2 g, 13.2 mmoi) in DMSO (6.6 mL) was added l 02 (1.6 mL) and K2C03 (274 mg, 1.98 mmoi). The resulting solution was stirred for 30 mm at it. The reaction was then quenched with NaHC03 (said, 30 mL). The resulting solution was extracted with EtO Ac (50 mL), and the organic layers were combined, and concentrated under reduced pressure. The residue was purified by flash column chromatography (0-10% EtO Ac/petroleum ether) on silica gel to obtain compound 36a as a white solid. ^I-NM (400 MHz, DMSQ-t δ (ppm): 7.66 - 7.70 (m, 2H), 7.04 - 7.23 (m, 3H), 3.77 (s, 3H)
With dihydrogen peroxide; potassium carbonate; In dimethyl sulfoxide; at 20.0℃; for 0.5h; To a solution of 2-fluoro-5--rnethoxybenzonitrile (2 g, 13.2 mmol) in DMSO (6.6 mL) was added H202 (1.6 mL) and K2C03 (274 mg, 1.98 mmol). The resulting solution was stirredfor 30 mm at rt. The reaction was then quenched with NaHCO3 (satd, 30 mL). The resulting solution was extracted with EtOAc (50 mL), and the organic layers were combined, and concentrated under reduced pressure. The residue was purified by flash column chromatography (0l0% EtOAc/petroleum ether) on silica gel to obtain compound 36a as a white solid. ‘H-NMR (400 M1-iz, DMSO-d6) (ppm): 7.66 7.70 (m, 21-1), 7.047.23 (m, 3H), 3.77 (s, 3M)
  • 8
  • [ 400-92-0 ]
  • ethyl 3-(2-fluoro-5-methoxyphenyl)isothiazole-5-carboxylate [ No CAS ]
  • 9
  • [ 400-92-0 ]
  • [ 2757-23-5 ]
  • 5-(2-fluoro-5-methoxyphenyl)-1,3,4-oxathiazol-2-one [ No CAS ]
YieldReaction ConditionsOperation in experiment
In toluene; at 100.0℃; B. 5-(2-Fluoro-5-methoxyphenyl)-1,3,4-oxathiazol-2-one, 36b A mixture of 36a (2.86 g, 16.9 mmol) and chloro(chlorosulfanyl)methanone (3.29 g, 25.1 mmol) in toluene (50 mL) was stirred overnight at 100 qC in an oil bath. The resulting mixture was concentrated under reduced pressure. The residue was purified by flash column chromatography (0-20% EtOAc/petroleum ether) on silica gel to obtain compound 36b as a yellow solid. 1H-NMR (300 MHz, DMSO-d6) (ppm): 7.24 - 7.49 (m, 3H), 3.80 (s, 3H).
In toluene; at 100.0℃; A mixture of 36a (2.86 g, 16.9 mmoi) and chloro(chlorosulfanyl)methanone (3.29 g, 25.1 mmol) in toluene (50 mL) was stirred overnight at 100 C in an oil bath. The resulting mixture was concentrated under reduced pressure. The residue was purified by flash column chromatography (0-20% EtO Ac/petroleum ether) on silica gel to obtain compound 36b as a yellow solid. i-R (300 MHz, DMSO-6 δ (ppm): 7.24 - 7.49 (m, 3H), 3.80 (s, 3H)
In toluene; at 100.0℃; A mixture of 36a (2.86 g, 16.9 mmol) and chloro(chiorosulfanyi)methanone (3.29 g, 25.1 mmoi) in toluene (50 mL) was stirred overnight at 100 C in an oil bath. The resulting mixture was concentrated under reduced pressure. The residue was purified by flash column chromatography (0-20% EtOAc/petroleum ether) on silica gel to obtain compound36b as a yellow solid. 1-i-NMR (300 MHz, DMSO-d6) (ppm): 7.24 - 7.49 (ni, 3H). 3.80 (s, 3H)
 

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