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[ CAS No. 71783-54-5 ] {[proInfo.proName]}

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Chemical Structure| 71783-54-5
Chemical Structure| 71783-54-5
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Product Details of [ 71783-54-5 ]

CAS No. :71783-54-5 MDL No. :MFCD08444284
Formula : C9H8BrFO2 Boiling Point : -
Linear Structure Formula :- InChI Key :ZDQQNZRQRARBNB-UHFFFAOYSA-N
M.W : 247.06 Pubchem ID :12717580
Synonyms :

Calculated chemistry of [ 71783-54-5 ]      Expand+

Physicochemical Properties

Num. heavy atoms : 13
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.22
Num. rotatable bonds : 3
Num. H-bond acceptors : 3.0
Num. H-bond donors : 0.0
Molar Refractivity : 50.14
TPSA : 26.3 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : Yes
P-gp substrate : No
CYP1A2 inhibitor : Yes
CYP2C19 inhibitor : No
CYP2C9 inhibitor : No
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -5.89 cm/s

Lipophilicity

Log Po/w (iLOGP) : 2.44
Log Po/w (XLOGP3) : 2.7
Log Po/w (WLOGP) : 2.53
Log Po/w (MLOGP) : 2.84
Log Po/w (SILICOS-IT) : 2.84
Consensus Log Po/w : 2.67

Druglikeness

Lipinski : 0.0
Ghose : None
Veber : 0.0
Egan : 0.0
Muegge : 0.0
Bioavailability Score : 0.55

Water Solubility

Log S (ESOL) : -3.22
Solubility : 0.15 mg/ml ; 0.000608 mol/l
Class : Soluble
Log S (Ali) : -2.91
Solubility : 0.307 mg/ml ; 0.00124 mol/l
Class : Soluble
Log S (SILICOS-IT) : -3.66
Solubility : 0.0542 mg/ml ; 0.000219 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 1.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 2.3

Safety of [ 71783-54-5 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P261-P280-P301+P312-P302+P352-P305+P351+P338 UN#:N/A
Hazard Statements:H302-H315-H319-H335 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 71783-54-5 ]

* 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 [ 71783-54-5 ]

[ 71783-54-5 ] Synthesis Path-Downstream   1~65

  • 1
  • [ 354-38-1 ]
  • [ 71783-54-5 ]
  • (4-Fluoro-phenyl)-(2,2,2-trifluoro-acetylamino)-acetic acid methyl ester [ No CAS ]
  • 2
  • [ 34837-84-8 ]
  • [ 71783-54-5 ]
YieldReaction ConditionsOperation in experiment
62% With sodium bromate; sodium hydrogensulfite; In water; ethyl acetate; at 20℃; for 6h; According to the method of Y. Ishii et al (J. Org. Chem. 1998, 63, 6023), a solution of (4-Fluoro-phenyl)-acetic acid methyl ester (25 g, 0.15 mol) in ethyl acetate (300 mL) was added to an aqueous sodium bromate solution (67 g; 0.45 mol in 225 mL water). The biphasic mixture was treated with 1M NaHSO3 (450 mL) and the reaction was allowed to stir at ambient temperature for 6 h. The phases were separated, the organic layer was washed with NaOH and Sat. NH4Cl, dried (Na2SO4), and concentrated to give a yellow oil. Residual starting material was removed by vacuum distillation (75 C., <0.11 mm Hg); yield: 22.6 g (62%); Low resolution mass spectroscopy (APCI) m/z 247/249 [M+H]+; 1H NMR (400 MHz, CDCl3): delta 3.8 (s, 3H), 5.3 (s, 1H), 7.0 (t, J=8.7 Hz, 2H), 7.5 (m, 2H).
With N-Bromosuccinimide; 2,2'-azobis(isobutyronitrile); In tetrachloromethane; at 20℃; for 72h;Reflux; Step A] Bromo-(4-fluoro-phenyl)-acetic Acid Methyl Ester; To a solution of methyl-4-fluorphenylacetate (10 g) in carbontetrachloride (80 mL) was added NBS (11.64 g) and AIBN (0.976 g) at RT. The reaction was then heated to reflux for 3 days. The reaction mixture was filtered and the solid washed with further carbontetrachloride. The filtrate was reduced in vacuo and the diluted with water (50 mL) and EtOAc (100 mL). The phases were separated and the aqueous phase was extracted with further EtOAc (100 mL). The combined organic phases were dried over sodium sulphate, filtered and evaporated in vacuo to afford the desired bromo-(4-fluoro-phenyl)-acetic acid methyl ester (15.0 g) as a yellow oil which was taken into the next step without further purification.
With N-Bromosuccinimide; In tetrachloromethane; at 80℃; for 3 - 4h;Heating / reflux; Example 5; To a dry MEOH solution (50 ML) containing 4-FLUOROPHENYLACETIC acid 5A (5 g, 0.0324 mole) was added a catalytic amount of 4-toluene sulfonicacid (0.324 mmole, 61 mg). The solution was refluxed for 4 h. The resultant solution was concentrated under reduced pressure to give pale-yellow syrup. The material was diluted with EtOAc (100 mL), and neutralized with NAHCO3 (1M, 5 mL). The organic layer was then washed with H20 (10 mLx2), followed by brine (10 mL), dried over MGS04 and filtered. The filtrate was concentrated to give a pale-yellow liquid. (5.33 g, 31.75 mmole, 98 %, MS M+H = 169 found: 169, 1H NMR structure confirmed). The methyl ester (2. 0g, 11.9 mmole) was then added to a CCL4 solution (100 mL) containing NBS (2.33 g, 13.09 mmole). The reaction mixture was refluxed at 80 C for 3 h to yield the brominated methyl ester 5b. The cooled solution was filtered through a pad of silica gel to remove excess SUCCINIMIDE, the filtrate was evaporated under reduced pressure, and the resultant material was transferred to the next reaction without further purification. To an acetonitrile solution containing the amine (TBIA, 2.44 g (8.94 mmole) /15 mL ACN) was added the compound 5B (ca. 2 g). While the reaction mixture was stirred triethylamine was added dropwise (1.70 ML, 12.2 mmole 1.5 equiv. ). The reaction mixture was stirred at ambient temperature for 16 h. After completion of the reaction, the reaction mixture was concentrated under reduced pressure, and diluted with EtOAc (25 mL). The organic layer was treated with H2O, dried over MGS04, and filtered. The filtrate was then concentrated under reduced pressure to give the compound 5c, 3.29 g. Isobutyryl chloride (0.53 ML, 4.99 mmole in 5 mL DCM) was added dropwise to a chilled DCM solution (10 mL) containing the compound 5C (2.0 g, 4.54 mmole). While the reaction mixture was stirred, a triethylamine solution (1.27 ML, 2 equiv. in 5 mL DCM) was added dropwise. The reaction mixture was agitated as it was warmed to room temperature for 2 h. After completion of the reaction, the reaction mixture was treated with IN HCL (20 mL), followed by sat. NAHC03 (3 mL). The organic layer was then washed with water and brine, dried over MGS04, and filtered. The filtrate was concentrated under reduced pressure to give pale-yellow syrup. This was purified by a column chromatography using a gradient of EtOAc-Hexane mixture (from 0 to 25 % of EtOAc). The isolated yield of the methyl ester was 2.10 g, 4.13 mmole, 90.9 %. The methyl ester (250 mg, 0.50 mmole) was dissolved in a LIOH solution (1M, THF : water (5: 1) mixture), and vigorously stirred for 3 h. The reaction mixture was neutralized to pH 7 by titrating it with 1N HCL solution. The desired product was then extracted with EtOAc (20 mL). The organic layer was washed with H2O and brine, dried over MgS04, and filtered. The filtrate was then evaporated under reduced pressure to give a white amorphous material 5 (200 mg, 0.40 mmole, 80 %, MS M+H = 496 found: 496, LU NMR structure confirmed).; Intermediate 2; Solution of 25.5 g (0.15 mol) of intermediate 1 in 50 ml of carbon tetrachloride was treated with 29.7 g (0.167 mol) of N-bromosuccinimide in 50 ml of carbon tetrachloride. Mixture was treated with 12 drops of HBR/HOAC (30%) and stirred at reflux for 2h. Treated with another 5 g (0.03 mol) of N- bromosuccinimide and stirred at reflux for 2h. Cooled and reaction was filtered through a mixture of magnesium sulfate/silica gel (1: 1). Concentrated to yield 36.89 g of liquid.
  • 3
  • [ 71783-54-5 ]
  • [ 292638-85-8 ]
  • [ 77053-69-1 ]
  • 4
  • [ 694-55-3 ]
  • [ 71783-54-5 ]
  • N-methyl-N-((methoxycarbonyl)methyl(p-fluorophenyl))-3,4-didehydropiperidinium bromide [ No CAS ]
  • 5
  • [ 71783-54-5 ]
  • [ 57260-71-6 ]
  • [ 191033-99-5 ]
  • 7
  • [ 71783-54-5 ]
  • 1-[2-(3,5-bis-trifluoromethyl-benzyloxy)-1-(4-fluoro-phenyl)-ethyl]-piperazine [ No CAS ]
  • 8
  • [ 71783-54-5 ]
  • 4-[2-(3,5-bis-trifluoromethyl-benzyloxy)-1-(4-fluoro-phenyl)-ethyl]-piperazine-1-carboxylic acid <i>tert</i>-butyl ester [ No CAS ]
  • 9
  • [ 71783-54-5 ]
  • cis-N-methyl-2-methoxycarbonyl-2-(p-fluorophenyl)-3-ethenylpyrrolidine [ No CAS ]
  • 10
  • [ 405-50-5 ]
  • [ 71783-54-5 ]
YieldReaction ConditionsOperation in experiment
71% With thionyl chloride; anhydrous phosphorus trichloride; bromine; In methanol; N,N-dimethyl-formamide; benzene; (RS) Methyl 2-bromo-2-(4-fluorophenyl)acetate STR61 4-Fluorophenylacetic acid (30.6 g), phosphorus trichloride (2 g) and bromine (36 g) in benzene (100 ml) were refluxed for 2 days, cooled, thionyl chloride (47 g) and N,N-dimethylformamide (0.2 g) were then added, the reaction mixture was refluxed for 1 hour, cooled, and methanol (100 ml) added. This mixture was refluxed for 1/2 hour, cooled, evaporated under reduced pressure and the residue distilled to give the title compound as a clear liquid (35 g, 71%), b.p. 104 C./2 mm.Hg. 1 H-N.M.R. (300 MHz, CDCl3) delta=3.8 (3H, s); 5.35 (s, 1H); 7.1 (m, 2H); 7.55 (m, 2H).
71% With thionyl chloride; anhydrous phosphorus trichloride; bromine; In methanol; N,N-dimethyl-formamide; benzene; (RS) Methyl 2-bromo-2-(4-fluorophenyl)acetate 4-Fluorophenylacetic acid (30.6 g), phosphorus trichloride (2 g) and bromine (36 g) in benzene (100 ml) were refluxed for 2 days, cooled, thionyl chloride (47 g) and N,N-dimethylformamide (0.2 g) were then added, the reaction mixture was refluxed for 1 hour, cooled, and methanol (100 ml) added. This mixture was refluxed for 1/2 hour, cooled, evaporated under reduced pressure and the residue distilled to give the title compound as a clear liquid (35 g, 71%), b.p. 104o/2 mm.Hg. 1H-N.M.R . (300 MHz, CDCl3) delta = 3.8 (3H, s); 5.35 (s, 1H); 7.1 (m, 2H); 7.55 (m, 2H).
  • 11
  • [ 71783-54-5 ]
  • [ 86215-41-0 ]
  • 12
  • [ 71783-54-5 ]
  • [ 66504-49-2 ]
  • 13
  • [ 71783-54-5 ]
  • [ 77053-79-3 ]
  • 14
  • [ 71783-54-5 ]
  • [ 7292-73-1 ]
  • 15
  • [ 71783-54-5 ]
  • [ 125971-86-0 ]
  • [ 845280-54-8 ]
YieldReaction ConditionsOperation in experiment
95% With triethylamine; In acetonitrile; at 20℃; A solution of [(4R,6R)-6-(2-Amino-ethyl)-2,2-dimethyl-[1,3]dioxan-4-yl]-acetic acid tert-butyl ester (26.3 g; 96 mmol) and bromo-(4-fluoro-phenyl)-acetic acid methyl ester (22.6 g; 92 mmol) in acetonitrile (200 mL) was treated with triethylamine (18.5 g; 182 mmol). After 30 minutes a considerable precipitate was noted. The reaction was allowed to stir at rt overnight then filtered to remove the precipitate. The filtrate was concentrated to dryness. The residue was dissolved in EtOAc, washed with H2O and brine, dried (MgSO4), and concentrated to give a crude oil. The oil was triturated with hexanes to give a white solid which was collected by vacuum filtration and air dried; yield: 38.1 g (95percent); Low resolution mass spectroscopy (APCI) m/z 440 [M+H]+.
With triethylamine; In acetonitrile; at 20℃; for 16h; Example 5; To a dry MEOH solution (50 ML) containing 4-FLUOROPHENYLACETIC acid 5A (5 g, 0.0324 mole) was added a catalytic amount of 4-toluene sulfonicacid (0.324 mmole, 61 mg). The solution was refluxed for 4 h. The resultant solution was concentrated under reduced pressure to give pale-yellow syrup. The material was diluted with EtOAc (100 mL), and neutralized with NAHCO3 (1M, 5 mL). The organic layer was then washed with H20 (10 mLx2), followed by brine (10 mL), dried over MGS04 and filtered. The filtrate was concentrated to give a pale-yellow liquid. (5.33 g, 31.75 mmole, 98 percent, MS M+H = 169 found: 169, 1H NMR structure confirmed). The methyl ester (2. 0g, 11.9 mmole) was then added to a CCL4 solution (100 mL) containing NBS (2.33 g, 13.09 mmole). The reaction mixture was refluxed at 80 °C for 3 h to yield the brominated methyl ester 5b. The cooled solution was filtered through a pad of silica gel to remove excess SUCCINIMIDE, the filtrate was evaporated under reduced pressure, and the resultant material was transferred to the next reaction without further purification. To an acetonitrile solution containing the amine (TBIA, 2.44 g (8.94 mmole) /15 mL ACN) was added the compound 5B (ca. 2 g). While the reaction mixture was stirred triethylamine was added dropwise (1.70 ML, 12.2 mmole 1.5 equiv. ). The reaction mixture was stirred at ambient temperature for 16 h. After completion of the reaction, the reaction mixture was concentrated under reduced pressure, and diluted with EtOAc (25 mL). The organic layer was treated with H2O, dried over MGS04, and filtered. The filtrate was then concentrated under reduced pressure to give the compound 5c, 3.29 g. Isobutyryl chloride (0.53 ML, 4.99 mmole in 5 mL DCM) was added dropwise to a chilled DCM solution (10 mL) containing the compound 5C (2.0 g, 4.54 mmole). While the reaction mixture was stirred, a triethylamine solution (1.27 ML, 2 equiv. in 5 mL DCM) was added dropwise. The reaction mixture was agitated as it was warmed to room temperature for 2 h. After completion of the reaction, the reaction mixture was treated with IN HCL (20 mL), followed by sat. NAHC03 (3 mL). The organic layer was then washed with water and brine, dried over MGS04, and filtered. The filtrate was concentrated under reduced pressure to give pale-yellow syrup. This was purified by a column chromatography using a gradient of EtOAc-Hexane mixture (from 0 to 25 percent of EtOAc). The isolated yield of the methyl ester was 2.10 g, 4.13 mmole, 90.9 percent. The methyl ester (250 mg, 0.50 mmole) was dissolved in a LIOH solution (1M, THF : water (5: 1) mixture), and vigorously stirred for 3 h. The reaction mixture was neutralized to pH 7 by titrating it with 1N HCL solution. The desired product was then extracted with EtOAc (20 mL). The organic layer was washed with H2O and brine, dried over MgS04, and filtered. The filtrate was then evaporated under reduced pressure to give a white amorphous material 5 (200 mg, 0.40 mmole, 80 percent, MS M+H = 496 found: 496, LU NMR structure confirmed).; Intermediate 3; Solution of 44.87 g (0.164 mol) of amine (TBIA) in 180 ml of acetonitrile was treated with a solution of 36.89 g (0.149 mol) of intermediate 2 in 90 ml of acetonitrile. Mixture was treated with 31.2 ml (0.224 mol) of triethylamine dropwise and stirred overnight at room temperature. Reaction was concentrated and the residue taken up in ethyl acetate and washed with water (2x). Organics were dried over sodium sulfate, filtered, and concentrated to yield approximately 69 g of a thick oil. MS APCI+ 440.2 (M+1).
YieldReaction ConditionsOperation in experiment
87% Part 2. The alpha-bromo-4-fluorophenylacetic acid from Part 1 was dissolved in methanol (100 ml) and was added Dowex-50X-400 (2.7 g) to the solution. The mixture was refluxed for 6 hours and the resin was removed by filtering through Celite after cooling. The filtrate was evaporated to give an oily residue, which was purified by column chromatography on silica gel with elution by 1:9 ethyl acetate-hexane to afford methyl alpha-bromo-4-fluorophenylacetate (87% yield).
198.5 g (92%) Step B Methyl 2-bromo-2-(4-fluoro)phenylacetate A mixture of 150.4 g (0.872 mol) of4-fluorophenylacetyl chloride (from Example 58, Step A') and 174.5 g (1.09 mol) of bromine was irradiated at 40-50 C. with a quartz lamp for 5-hours. The reaction mixture was added dropwise to 400 mL of methanol and the solution was stirred for 16 hours. The solvent was removed in vacuo and the residual oil was distilled at reduced pressure (1.5 mmHg) to afford 198.5 g (92%) of the title compound, bp=106-110 C.
  • 17
  • [ 459-04-1 ]
  • [ 71783-54-5 ]
YieldReaction ConditionsOperation in experiment
198.5 g (92%) With bromine; In methanol; Step B' Methyl 2-bromo-2-(4-fluoro)phenylacetate A mixture of 150.4 g (0.872 mol) of 4-fluorophenylacetyl chloride and 174.5 g (1.09 mol) of bromine was irradiated at 40-50 C. with a quartz lamp for 5 hours. The reaction mixture was added dropwise to 400 mL of methanol and the solution was stirred for 16 hours. The solvent was removed in vacuo and the residual oil was distilled at reduced pressure (1.5 mmHg) to afford 198.5 g (92%) of the title compound, bp=106-110 C.
198.5 g (92%) With bromine; In methanol; Step B': Methyl 2-bromo-2-(4-fluoro)-phenylacetate A mixture of 150.4 g (0.872 mol) of 4-fluorophenylacetyl chloride (from Example 58, Step A') and 174.5 g (1.09 mol) of bromine was irradiated at 40-50 C. with a quartz lamp for 5 hours. The reaction mixture was added dropwise to 400 mL of methanol and the solution was stirred for 16 hours. The solvent was removed in vacuo and the residual oil was distilled at reduced pressure (1.5 mmHg) to afford 198.5 g (92%) of the title compound, bp=106-110 C.
198.5 g (92%) With bromine; In methanol; Step B' Methyl 2-bromo-2-(4-fluoro)phenylacetate A mixture of 150.4 g (0.872 mol) of 4-fluorophenylacetyl chloride (from Example 58, Step A') and 174.5 g (1.09 mol) of bromine was irradiated at 40-50 C. with a quartz lamp for 5 hours. The reaction mixture was added dropwise to 400 mL of methanol and the solution was stirred for 16 hours. The solvent was removed in vacuo and the residual oil was distilled at reduced pressure (1.5 mmHg) to afford 198.5 g (92%) of the title compound, bp=106-110 C.
198.5 g (92%) With bromine; In methanol; Step B': Methyl 2-bromo-2-(4-fluoro)phenylacetate A mixture of 150.4 g (0.872 mol) of 4-fluorophenylacetyl chloride (from Example 58, Step A') and 174.5 g (1.09 mol) of bromine was irradiated at 40-50 C. with a quartz lamp for 5 hours. The reaction mixture was added dropwise to 400 mL of methanol and the solution was stirred for 16 hours. The solvent was removed in vacuo and the residual oil was distilled at reduced pressure (1.5 mmHg) to afford 198.5 g (92%) of the title compound, bp=106-110 C.

  • 18
  • [ 71783-54-5 ]
  • [ 137-07-5 ]
  • [ 100638-27-5 ]
YieldReaction ConditionsOperation in experiment
With sodium acetate; In ethanol; water; Reference Example 1 To a suspension of 2-aminothiophenol (12.6 g) and sodium acetate (23.6 g) in ethanol (150 ml) is added methyl alpha-bromo-4-fluorophenylacetate (23.6 g), and the mixture is stirred at room temperature overnight. After the solvent is distilled off, water is added to the residue. The resulting precipitate is separated by filtration, washed, dried, and then recrystallized from tetrahydrofuran-n-hexane to give 2-(4-fluorophenyl)-3-oxo-3,4-dihydro-2H-1,4-benzothiazine (21.7 g) as crystals. M.p. 216-219 C.
  • 19
  • [ 15894-04-9 ]
  • [ 71783-54-5 ]
  • [ 6674-22-2 ]
  • [ 186025-96-7 ]
YieldReaction ConditionsOperation in experiment
With hydrogenchloride; In dichloromethane; Part 3. To a stirred solution of methyl alpha-bromo-4-fluorophenylacetate (1 g) and 4-fluorobenzylthiol (0.69 g) in dry methylene chloride (10 ml) was added 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU, 0.91 ml) dropwise, and the mixture was stirred for 30 minutes at room temperature After cooling to 0, 7 ml of 1N HCl was added dropwise and the product was extracted with ethyl ether. The extract was washed with water and brine, dried (magnesium sulfate) and evaporated to give an oily residue. Column chromatography on silica gel with elution by 5:95 ethyl acetate-hexane provided pure methyl alpha-(4-fluoro)-benzylthio-4-fluorophenylacetate (0.75 g), a compound of Formula 4 wherein, X is S, R5 is 4-fluorophenyl and R7 is 4-fluoro-benzyl.
  • 20
  • [ 111-31-9 ]
  • [ 71783-54-5 ]
  • [ 186025-94-5 ]
YieldReaction ConditionsOperation in experiment
With ammonium chloride; In tetrahydrofuran; Part 3. To a stirred suspension of sodium hydride (0.114 g) in dry tetrahydrofuran (15 ml) was added hexanethiol (0.69 ml) dropwise, and the mixture was stirred for 1 hour at room temperature. Then a solution of methyl alpha-bromo-4-fluorophenylacetate (1 g) in tetrahydrofuran (15 ml) was added dropwise, and the mixture was stirred for 5 hours at room temperature. The reaction was quenched with saturated ammonium chloride and the product was extracted with ethyl ether. The extract was washed with water and brine, dried (magnesium sulfate) and evaporated to give an oily residue. Column chromatography on silica gel with elution by 5:95 ethyl acetate-hexane provided pure methyl alpha-hexylthio-4-fluorophenylacetate (0.7 g), a compound of Formula 4 wherein, X is S, R5 is 4-fluorophenyl and R7 is hexyl.
  • 21
  • [ 71783-54-5 ]
  • [ 122-52-1 ]
  • [ 1397007-09-8 ]
  • 22
  • [ 71783-54-5 ]
  • [ 156-87-6 ]
  • [ 1194032-78-4 ]
YieldReaction ConditionsOperation in experiment
With potassium carbonate; In chloroform; at 45℃; for 18h; Step B] (4-Fluoro-phenyl)-(3-hydroxy-propylamino)-acetic Acid Methyl Ester; To a solution of <strong>[71783-54-5]bromo-(4-fluoro-phenyl)-acetic acid methyl ester</strong> (16.0 g) in chloroform (100 mL) was added potassium carbonate (17.9 g, finely ground) followed by 3-amino-1-propanol (4.87 g). The reaction was heated to 45 C. for 18 hours. The reaction was filtered and the filtrate was diluted with water and the phases were separated. The aqueous phase was further extracted with chloroform (3×25 mL) and the combined organics were washed with brine. The chloroform phase was dried over sodium sulfate, filtered and evaporated in vacuo to give the desired (4-fluoro-phenyl)-(3-hydroxy-propylamino)-acetic acid methyl ester (14.85 g, MS (ES+): 242.2 (MH+)) as a yellow oil which was used in the next step without further purification.
  • 23
  • [ 592542-50-2 ]
  • [ 71783-54-5 ]
  • [ 1330633-94-7 ]
  • 24
  • [ 110-89-4 ]
  • [ 71783-54-5 ]
  • [ 1142290-55-8 ]
YieldReaction ConditionsOperation in experiment
58.5% With N-ethyl-N,N-diisopropylamine; In acetonitrile; at 20℃; for 3h; Preparation of methyl 2-(4-fluorophenyl)-2-(piperidin-l- yl)acetate (196). Methyl 2-bromo-2-(4-fluorophenyl)acetate (538 mg, 2.18 mmol) was dissolved in CH3CN (6.6 ml) and piperidine (258 mu, 2.61 mmol) and N-ethyl-N-isopropylpropan-2-amine (456 mu, 2.61 mmol) were added sequentially. The solution was stirred at room temperature for 3 h, then the solvent was evaporated and the crude was purified with flash chromatography (Petroleum ether/EtOAc= 9/1) to collect methyl 2-(4- fluorophenyl)-2-(piperidin- l-yl)acetate (320 mg, 58.5 % yield) as a colourless oil.
58.5% With N-ethyl-N,N-diisopropylamine; In acetonitrile; at 20℃; for 3h; Preparation of methyl 2-(4-fluorophenyl)-2-(piperidin-1-yl)acetate (I96) Methyl 2-bromo-2-(4-fluorophenyl)acetate (538 mg, 2.18 mmol) was dissolved in CH3CN (6.6 ml) and piperidine (258 mul, 2.61 mmol) and N-ethyl-N-isopropylpropan-2-amine (456 mul, 2.61 mmol) were added sequentially. The solution was stirred at room temperature for 3 hours, then the solvent was evaporated and the crude was purified with flash chromatography (Petroleum ether/EtOAc=9/1) to collect methyl 2-(4-fluorophenyl)-2-(piperidin-1-yl)acetate (320 mg, 58.5% yield) as a courless oil.
  • 25
  • [ 595582-49-3 ]
  • [ 71783-54-5 ]
  • [ 1445726-87-3 ]
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  • [ 71783-54-5 ]
  • [ 1260641-65-3 ]
  • 27
  • [ 71783-54-5 ]
  • [ 1446308-41-3 ]
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  • [ 1446308-42-4 ]
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  • [ 1446308-43-5 ]
  • 30
  • [ 1584657-18-0 ]
  • [ 71783-54-5 ]
  • C28H32FNO8S [ No CAS ]
YieldReaction ConditionsOperation in experiment
With sodium acetate; In ethanol; for 48.17h;Reflux; The title compound is prepared according to Scheme 6. Sodium acetate (32.8 g, 400 mmol) is dissolved in ethanol (200 mL). 2-bromo-2-(4-fluorophenyl)acetate (400 mmol) is added to the above solution and refluxed for 10 min. To the cooled reaction mixture compound 2-methoxy-5-(((2,4,6-trimethoxyphenethyl) sulfonyl)methyl)aniline (39.35 g, 100 mmol) is added and then refluxed for 48 h. After completion of the reaction monitored by TLC (chloroform/ methanol, 9: 1 on silica gel plate), the reaction mixture is concentrated under vacuum and poured into ice-water. The solid formed is filtered, washed with water, and dried under vacuum. The crude product on purification from ethanol results in analytical pure product.
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  • [ 95-54-5 ]
  • [ 122340-51-6 ]
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  • [ 1634722-00-1 ]
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  • [ 1634721-94-0 ]
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  • [ 1057221-63-2 ]
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  • [ 1634722-01-2 ]
  • 39
  • [ 71783-54-5 ]
  • [ 1634721-96-2 ]
  • 40
  • [ 71783-54-5 ]
  • [ 1634722-03-4 ]
  • 41
  • [ 71783-54-5 ]
  • [ 89108-49-6 ]
  • methyl 7-fluoro-2-(p-tolyl)quinoline-4-carboxylate [ No CAS ]
  • 42
  • [ 71783-54-5 ]
  • [ 285984-22-7 ]
  • 2-((4-(((tert-butoxy)carbonyl)amino)naphthalen-1-yl)oxy)(4-fluorophenyl)acetic acid methyl ester [ No CAS ]
YieldReaction ConditionsOperation in experiment
20.7% With potassium carbonate; In N,N-dimethyl-formamide; at 20℃; for 2h; The 1-hydroxy-4-nitronaphthalenesulfonic (2.8g, 14 . 8mmol) dissolved in methanol, added 5% palladium-carbon (78.0 mg, 0 . 8mmol), the balloon meets the hydrogen, reaction at room temperature. board detection reaction is complete, oil filtration to palladium-carbon, adding the filtrate (Boc)2O (6.5g. 29 . 7mmol), triethylamine (4.1 ml, 29 . 7mmol), N2protection, stirring at room temperature. board display the reaction is complete, turns on lathe does methanol, dissolved with ethyl acetate, pH3-4 a dilute hydrochloric acid solution washing 3 times, combined with the organic layer, shall turns on lathe does grey solid, without processing, dissolved in the 10mlDMF in, by adding 4-fluoro-alpha-bromo acetic acid methyl ester (4.39g, 17 . 8mmol) and potassium carbonate (3.07g, 22 . 2mmol) reaction at room temperature. board display the reaction is complete (about 2h), water, extraction EA 3 time, combined with the organic layer, using saturated ammonium chloride washing 3 times, saturated sodium chloride washing 3 times, PE sha Yongturns on lathe does the system : EA=8:1 the separation and purification by silica gel column to obtain orange solid 1.3 g. The yield is 20.7%
  • 43
  • tert-butyl 4-(3-amino-5-methoxyphenoxy)butanoate [ No CAS ]
  • [ 71783-54-5 ]
  • tert-butyl 4-(3-((1-(4-fluorophenyl)-2-methoxy-2-oxoethyl)amino)-5-methoxyphenoxy)butanoate [ No CAS ]
YieldReaction ConditionsOperation in experiment
0.511 g With triethylamine; In acetonitrile; at 100℃; for 0.333333h;Microwave irradiation; A mixture of <strong>[71783-54-5]methyl 2-bromo-2-(4-fluorophenyl)acetate</strong> [CAS 71783-54-5] (0.400 g, 1 .62 mmol), te/t-butyl 4-(3-amino-5-methoxyphenoxy)butanoate 1a (0.547 g, 1 .94 mmol) and triethylamine (0.337 mL, 2.43 mmol) in CH3CN (4 mL) was heated in a microwave oven at 100C for 20 min. The reaction mixture was diluted with EtOAc and washed with 1 N HCI. The organic phase was washed with H2O and brine, dried over MgSO4, filtered and concentrated under reduced pressure. The residue was purified by flash chromatography on silica gel using a gradient of EtOAc (2% to 20%) in heptane to give terf-butyl 4-(3-((1 -(4-fluorophenyl)-2- methoxy-2-oxoethyl)amino)-5-methoxyphenoxy)butanoate 1b (0.51 1 g).
  • 44
  • 2-(dimethylamino)-4-ethyl-6-mercaptopyridine-3,5-dicarbonitrile [ No CAS ]
  • [ 71783-54-5 ]
  • methyl 2-((3,5-dicyano-6-(dimethylamino)-4-ethylpyridin-2-yl)thio)-2-(4-fluorophenyl)acetate [ No CAS ]
YieldReaction ConditionsOperation in experiment
400 mg With triethylamine; In N,N-dimethyl-formamide; at 25℃; To a solution of 2-(dimethylamino)-4-ethyl-6-mercaptopyridine-3,5-dicarbonitrile (692 mg, 2.98 mmol) in N,N-dimethylformamide (50 mL) was added methyl 2-bromo-2-(4- fluorophenyl)acetate (736 mg, 2.98 mmol) and triethylamine (302 mg, 2.98 mmol). The reaction was stirred at 25 C overnight. The mixture was partially evaporated and the residue was added to ice water. The resulting solid was collected by filtration to give methyl 2-((3,5-dicyano-6-(dimethylamino)-4-ethylpyridin-2-yl)thio)-2-(4-fluorophenyl)acetate (400 mg, 34% yield) as a white solid. LCMS m/z = 399 [M+H]+.
  • 45
  • tert-butyl 4-(3,5-dicyano-4-ethyl-6-mercaptopyridin-2-yl)piperazine-1-carboxylate [ No CAS ]
  • [ 71783-54-5 ]
  • C27H30FN5O4S [ No CAS ]
YieldReaction ConditionsOperation in experiment
74% With triethylamine; In dichloromethane; at 25℃; To a solution of tert-butyl 4-(3,5-dicyano-4-ethyl-6-mercaptopyridin-2-yl)piperazine-1- carboxylate (400 mg, 1.071 mmol) in dichloromethane (150 mL) was added methyl 2- bromo-2-(4-fluorophenyl)acetate (265 mg, 1.071 mmol) and triethylamine (108 mg, 1.071 mmol). The reaction mixture was stirred at 25 C overnight. The reaction was concentrated and the residue was loaded on a silica gel column which was eluted with hexane/EtOAc to give tert-butyl 4-(3,5-dicyano-4-ethyl-6-(1-(4-fluorophenyl)-2-methoxy-2-oxoethyl)pyridin- 2-yl)piperazine-1-carboxylate (400 mg, 74% yield). LCMS m/z = 407 [M-Boc+H]+.
  • 46
  • [ 127709-19-7 ]
  • [ 71783-54-5 ]
YieldReaction ConditionsOperation in experiment
85% With phosphorus tribromide; In chloroform; at 20℃; for 96h; General procedure: Methyl 2-hydroxy-2-phenylacetate 7a (5.00 g, 30 mmol) was dissolved in CHCl3 (50 ml) and 2 equivalents of PBr3 (8.09 ml, 60 mmol). This was then stirred at r.t. for 4 days. Upon completion the reaction was washed with water (50 ml), dried (MgSO4) and then passed through a silica pad. The CHCl3 was removed to give the title compound as a clear oil, 5.00 g (26 mmol, 75%).
  • 47
  • [ 71783-54-5 ]
  • methyl 2-(4-fluorophenyl)-mercaptoacetate [ No CAS ]
  • 48
  • [ 71783-54-5 ]
  • 2-(4-fluorophenyl)-2-mercaptoacetic acid [ No CAS ]
  • 49
  • [ 71783-54-5 ]
  • 4-(4-fluorophenyl)-1,3,2-oxathiazolium-5-olate [ No CAS ]
  • 50
  • [ 71783-54-5 ]
  • C8H6FNO3S [ No CAS ]
  • 51
  • [ 71783-54-5 ]
  • C8H4FNO2S [ No CAS ]
  • 52
  • [ 71783-54-5 ]
  • [ 10387-40-3 ]
  • [ 1186200-76-9 ]
YieldReaction ConditionsOperation in experiment
99% In methanol; at 20℃; for 4h; General procedure: Potassium thioacetate (2.0 g, 17 mmol) was added to methyl 2-bromo-2-phenylacetate 8a (2.0 g, 8.9 mmol) dissolved in methanol (50 ml). The solution was stirred at r.t. for 4 hours and the KBr salt was then filtered off, before the filtrate was reduced to give the title compound as a light orange oil, 1.90 g (8.4 mmol, 95%).
  • 54
  • [ 71783-54-5 ]
  • [ 88-75-5 ]
  • methyl 2-(4-fluorophenyl)-2-(2-nitrophenoxy)acetate [ No CAS ]
  • 55
  • [ 71783-54-5 ]
  • N-t-butoxycarbonyl-2-(4-fluorophenyl)-1,4-benzoxazin-3-one [ No CAS ]
  • 56
  • [ 71783-54-5 ]
  • C26H24FNO4 [ No CAS ]
  • 57
  • [ 71783-54-5 ]
  • C14H10FNO2 [ No CAS ]
  • 58
  • [ 71783-54-5 ]
  • methyl (2S,3R)-2-(4-fluorophenyl)-2-nitro-3-phenylpent-4-ynoate [ No CAS ]
  • methyl 2-(4-fluorophenyl)-2-nitro-3-phenylpent-4-ynoate [ No CAS ]
  • 59
  • [ 71783-54-5 ]
  • methyl 2-(4-fluorophenyl)-2-nitroacetate [ No CAS ]
  • 60
  • [ 67-56-1 ]
  • [ 29270-33-5 ]
  • [ 71783-54-5 ]
  • 61
  • [ 71783-54-5 ]
  • tert-butyl (2S,5R)-4-(1-(4-fluorophenyl)-2-hydroxyethyl)-2,5-dimethylpiperazine-1-carboxylate [ No CAS ]
  • 62
  • [ 71783-54-5 ]
  • tert-butyl (2S,5R)-4-(1-(4-fluorophenyl)-2-hydroxy-2-methylpropyl)-2,5-dimethylpiperazine-1-carboxylate [ No CAS ]
  • 63
  • [ 71783-54-5 ]
  • 1-((2R,5S)-2,5-dimethylpiperazin-1-yl)-1-(4-fluorophenyl)-2-methylpropan-2-ol trifluoroacetate [ No CAS ]
  • 64
  • [ 71783-54-5 ]
  • 8-((2S,5R)-4-((1R)-1-(4-fluorophenyl)-2-hydroxy-2-methylpropyl)-2,5-dimethylpiperazin-1-yl)-5-methyl-6-oxo-5,6-dihydro-1,5-naphthyridine-2-carbonitrile [ No CAS ]
  • 8-((2S,5R)-4-((1S)-1-(4-fluorophenyl)-2-hydroxy-2-methylpropyl)-2,5-dimethylpiperazin-1-yl)-5-methyl-6-oxo-5,6-dihydro-1,5-naphthyridine-2-carbonitrile [ No CAS ]
  • 65
  • [ 71783-54-5 ]
  • [ 548762-66-9 ]
  • tert-butyl (2S,5R)-4-(1-(4-fluorophenyl)-2-methoxy-2-oxoethyl)-2,5-dimethylpiperazine-1-carboxylate [ No CAS ]
YieldReaction ConditionsOperation in experiment
88% With N-ethyl-N,N-diisopropylamine; In acetonitrile; at 85℃; for 16h; To a stirred solution of <strong>[548762-66-9]tert-butyl (2S,5R)-2,5-dimethylpiperazine-1-carboxylate</strong> (1.5 g, 7. mmol) in acetonitrile (15 mL) was added DIPEA (3.7 mL, 21 mmol) and methyl 2-bromo-2-(4-fluorophenyl)acetate (1.9 g, 7.7 mmol). The reaction mixture was heated up to 85 C over 10 min and was stirred for 16 h. The reaction mixture was concentrated under reduced pressure to obtain a brown gummy solid. The crude compound was purified by flash chromatography (using 24 g silica gel column; using 5 % -10 % ethylacetate/ Pet. ether) to obtain tert-butyl (2S,5R)-4-(1-(4-fluorophenyl)-2-methoxy-2- oxoethyl)-2,5-dimethylpiperazine-1-carboxylate (2.35 g, 6.18 mmol, 88% yield) as brown solid. LCMS: m/z, 379.3 (M-H); rt 1.13 min; Column: Waters Acquity UPLC BEH C18 (2.1 x 50 mm) 1.7 mm, Mobile phase A: 10 mM ammonium acetate:acetonitrile (95:5); Mobile phase B: 10 mM ammonium acetate:acetonitrile (5:95), Gradient = 20-90 % B over 1.1 minute, then a 0.6 minute hold at 90 % B; Temperature: 50 C; Flow rate: 0.7 mL/min; Detection: UV at 220 nm.
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