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Product Details of [ 34837-84-8 ]

CAS No. :34837-84-8 MDL No. :MFCD00800608
Formula : C9H9FO2 Boiling Point : -
Linear Structure Formula :- InChI Key :AJPPKGMEHMXPMC-UHFFFAOYSA-N
M.W : 168.17 Pubchem ID :2733233
Synonyms :

Calculated chemistry of [ 34837-84-8 ]      Expand+

Physicochemical Properties

Num. heavy atoms : 12
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 : 42.27
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) : -5.96 cm/s

Lipophilicity

Log Po/w (iLOGP) : 2.17
Log Po/w (XLOGP3) : 1.93
Log Po/w (WLOGP) : 1.96
Log Po/w (MLOGP) : 2.4
Log Po/w (SILICOS-IT) : 2.45
Consensus Log Po/w : 2.18

Druglikeness

Lipinski : 0.0
Ghose : None
Veber : 0.0
Egan : 0.0
Muegge : 1.0
Bioavailability Score : 0.55

Water Solubility

Log S (ESOL) : -2.27
Solubility : 0.902 mg/ml ; 0.00536 mol/l
Class : Soluble
Log S (Ali) : -2.11
Solubility : 1.32 mg/ml ; 0.00783 mol/l
Class : Soluble
Log S (SILICOS-IT) : -3.15
Solubility : 0.119 mg/ml ; 0.000706 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.39

Safety of [ 34837-84-8 ]

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

Application In Synthesis of [ 34837-84-8 ]

* 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.

  • Upstream synthesis route of [ 34837-84-8 ]
  • Downstream synthetic route of [ 34837-84-8 ]

[ 34837-84-8 ] Synthesis Path-Upstream   1~17

  • 1
  • [ 405-50-5 ]
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YieldReaction ConditionsOperation in experiment
81% With hydrogenchloride In 1,4-dioxane; methanol for 18 h; Heating / reflux A solution of 2- (4-fluorophenyl) acetic acid (15.4 G, 0. 1 mol) in methanol (600 mL) was treated with a solution of hydrogen chloride in dioxane (4 N, 100 mL) followed by warming at reflux for 18 h. The solution was cooled and concentrated in vacuo. The residue was distilled under reduced pressure (55-58 °C/0. 5 mm Hg) to afford the title compound as colorless oil (13.6 g, 81percent).#x0;H NMR (300 MHZ, CDC13) : 8 3.60 (s, 2 H) 3.70 (s, 3 H) 7.02 (m, 2 H) 7.24 (m, 2 H).
Reference: [1] Patent: WO2005/19191, 2005, A2, . Location in patent: Page/Page column 147
[2] Patent: US6307047, 2001, B1,
[3] Patent: US5686455, 1997, A,
[4] Tetrahedron Letters, 2015, vol. 56, # 31, p. 4634 - 4637
[5] Angewandte Chemie - International Edition, 2018, vol. 57, # 12, p. 3233 - 3237[6] Angew. Chem., 2018, vol. 130, # 12, p. 3287 - 3291,5
[7] Patent: US5760018, 1998, A,
[8] Patent: US5519048, 1996, A,
  • 2
  • [ 67-56-1 ]
  • [ 405-50-5 ]
  • [ 34837-84-8 ]
YieldReaction ConditionsOperation in experiment
98% for 3 - 4 h; 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 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 1; A solution of 100 g (0.64 mol) OF 4-FLUOROPHENYLACETIC ACID, 0.5 g (2.6 mmol) of P-TOLUENESULFONIC acid in 600 ml of methanol was refluxed with stirring for 3h. After cooling, the reaction was concentrated and the residue taken up in ethyl acetate. Organics washed with a saturated NAHC03 solution, water, and brine. Dried over sodium sulfate, filtered, and concentrated to yield 101.5 grams of a clear liquid. MS AP+ 169.0 (M+1), AP-167.0 (M-1).
84% at 70℃; for 7 h; Reflux; Inert atmosphere Step 1: To the solution 2-(4-fluorophenyl)acetic acid (700 mg, 43.4 mmol) in methanol was slowly added sulfuric acid (0.42 mL,4.34 mmol,0.1 eq) at room temperature. The reaction mixture was refluxed for 3 h at 70° C. under N2 TLC showed complete consumption of starting material. The reaction mixture was cooled to room temperature. Solvent was removed in vacuo and extracted with ethyl acetate. The organic part was washed with brine. The organic layer was dried over magnesium sulfate and concentrated under reduced pressure to afford crude product which was purified by column chromatography to methyl 2-(4-fluorophenyl)acetate (660 mg, 84percent).
84% for 3 h; Reflux; Inert atmosphere Step 1 : To the solution 2-(4-fluorophenyl)acetic acid (700 mg, 43.4 mmol ) in methanol was slowly added sulfuric acid (0.42 ml_,4.34 mmol, 0.1 eq) at room temperature. The reaction mixture was refluxed for 3 h at 70 °C under N2. TLC showed complete consumption of starting material. The reaction mixture was cooled to room temperature. Solvent was removed in vacuo and extracted with ethyl acetate. The organic part was washed with brine. The organic layer was dried over magnesium sulfate and concentrated under reduced pressure to afford crude product which was purified by column chromatography to methyl 2- (4-fluorophenyl)acetate (660 mg, 84 percent).
81% With hydrogenchloride In 1,4-dioxane for 18 h; Heating / reflux EXAMPLE 14A
Methyl(4-fluorophenyl)acetate
A solution of 2-(4-fluorophenyl)acetic acid (15.4 g, 0.1 mol) in methanol (600 mL) was treated with a solution of hydrogen chloride in dioxane (4 N, 100 mL) followed by warming at reflux for 18 h.
The solution was cooled and concentrated in vacuo.
The residue was distilled under reduced pressure (55-58° C./0.5 mm Hg) to afford the title compound as colorless oil (13.6 g, 81percent).
1H NMR (300 MHz, CDCl3): δ 3.60 (s, 2H) 3.70 (s, 3H) 7.02 (m, 2H) 7.24 (m, 2H).
80% Reflux General procedure: To an appropriately substituted phenylacetic acid (10 mmol) dissolved in dried methanol (50 mL), concentrated sulfuric acid (0.5 mL) was added dropwise.The mixture was refluxed from 7 to 9 h. Next, the solvent was evaporated, and residue was dissolved in 40 mL of ethyl acetate, washed with 0.5percent NaOH andbrine. Organic layer was dried over anhydrous Na2SO4 and filtered. The solvent was evaporated to give the products as colorless oils.
75% for 16 h; Reflux 2-(4-Fluorophenyl)acetic acid 12c (5.00 g, 32.4 mmol) was dissolved in CH3OH (6.5 mL). Conc. H2SO4 (0.3 mL) was added and the mixture was headed to reflux overnight.
Water was added, the organic layer was separated and the aqueous layer was extracted with Et2O (3*).
The combined organic layers were washed with saturated aqueous NaHCO3 and water to remove the acid.
Then the organic layers were dried (Na2SO4), filtered and the solvent was removed under reduced pressure, Rf = 0.23 (CH2Cl2/EtOAc 40:60).
Colorless oil, yield 4.07 g (75percent). C9H9FO2 (168.2 g/mol).
1H NMR (CDCl3): δ [ppm] = 3.60 (s, 2H, PhCH2), 3.69 (s, 3H, CO2CH3), 6.96-7.05 (m, 2H, 3-Harom, 5-Harom), 7.19-7.28 (m, 2H, 2-Harom, 4-Harom).
13C NMR (CDCl3): δ [ppm] = 40.3 (1C, CH2), 52.1 (1C, CO2CH3), 115.4 (d, J = 21.3 Hz, 2C, C-3arom, C-5arom), 129.6 (d, J = 3.4 Hz, 1C, C-1arom), 130.8 (d, J = 8.0 Hz, 2C, C-2arom, C-6arom), 162.0 (d, J = 241.5 Hz, 1C, C-4arom), 174.9 (1C, C=O). MS (APCI): m/z = 169.0654 (calcd 169.0659 for C9H10FO2 [MH+]). IR: [cm-1] = 2955 (C-H), 1736 (C=O), 1153 (C-Farom), 822 (C-Harom).
22 g at 20℃; for 24 h; 20g of p-fluorophenylacetic acid was added to 400ml of methanol, Add 2 g of methylbenzenesulfonic acid, Stirred at room temperature for 24 hours, concentrate, Add water and ethyl acetate extraction, Liquid separation, dry, concentrate, The residue was separated on the column to give 22 g of methyl 2-(4-fluorophenyl)acetate.

Reference: [1] Bioorganic and Medicinal Chemistry, 2003, vol. 11, # 13, p. 2843 - 2866
[2] Bioorganic and Medicinal Chemistry, 2005, vol. 13, # 15, p. 4694 - 4703
[3] Bioorganic and Medicinal Chemistry Letters, 2008, vol. 18, # 3, p. 1151 - 1156
[4] Patent: WO2005/14539, 2005, A2, . Location in patent: Page/Page column 57-59; 68-69
[5] Tetrahedron, 2002, vol. 58, # 51, p. 10113 - 10126
[6] Organic letters, 2002, vol. 4, # 3, p. 371 - 373
[7] Journal of Organic Chemistry, 2009, vol. 74, # 6, p. 2598 - 2600
[8] Patent: US2013/79320, 2013, A1, . Location in patent: Paragraph 0668; 0669
[9] Patent: WO2013/45451, 2013, A1, . Location in patent: Page/Page column 102
[10] Journal of the American Chemical Society, 2015, vol. 137, # 32, p. 10246 - 10253
[11] Patent: US2005/107364, 2005, A1, . Location in patent: Page/Page column 74
[12] Journal of Organic Chemistry, 2016, vol. 81, # 15, p. 6808 - 6815
[13] European Journal of Medicinal Chemistry, 2017, vol. 135, p. 117 - 124
[14] Bioorganic and Medicinal Chemistry, 2015, vol. 23, # 14, p. 4034 - 4049
[15] Bioorganic and Medicinal Chemistry Letters, 2000, vol. 10, # 16, p. 1893 - 1895
[16] Tetrahedron, 2008, vol. 64, # 22, p. 5072 - 5078
[17] Organic Letters, 2010, vol. 12, # 17, p. 3736 - 3739
[18] Bulletin of the Korean Chemical Society, 2010, vol. 31, # 8, p. 2315 - 2321
[19] Comptes Rendus Chimie, 2011, vol. 14, # 12, p. 1071 - 1079
[20] Chemical Communications, 2012, vol. 48, # 79, p. 9936 - 9938
[21] Research on Chemical Intermediates, 2012, vol. 38, # 8, p. 1827 - 1837
[22] Bulletin of the Korean Chemical Society, 2012, vol. 33, # 12, p. 3943 - 3949
[23] Patent: WO2013/104829, 2013, A1, . Location in patent: Page/Page column 23; 24
[24] Bioorganic and Medicinal Chemistry Letters, 2014, vol. 24, # 7, p. 1677 - 1680
[25] Bioorganic and Medicinal Chemistry Letters, 2015, vol. 25, # 3, p. 481 - 484
[26] Advanced Synthesis and Catalysis, 2015, vol. 357, # 11, p. 2479 - 2484
[27] New Journal of Chemistry, 2016, vol. 40, # 7, p. 6109 - 6119
[28] Angewandte Chemie - International Edition, 2017, vol. 56, # 14, p. 3987 - 3991[29] Angew. Chem., 2017, vol. 129, # 14, p. 4045 - 4049,5
[30] Patent: WO2017/49069, 2017, A1, . Location in patent: Paragraph 00197
[31] Bioorganic and Medicinal Chemistry, 2017, vol. 25, # 14, p. 3719 - 3735
[32] Chemical Communications, 2017, vol. 53, # 75, p. 10429 - 10432
[33] Patent: CN107286069, 2017, A, . Location in patent: Paragraph 0023; 0024
[34] Journal of Chemistry, 2017, vol. 2017,
[35] Organic Letters, 2018, vol. 20, # 10, p. 2997 - 3000
[36] Organic Letters, 2018, vol. 20, # 24, p. 7888 - 7892
  • 3
  • [ 119114-45-3 ]
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YieldReaction ConditionsOperation in experiment
50% With 3-chloro-benzenecarboperoxoic acid; copper(ll) bromide In 1,4-dioxane at 70℃; for 3 h; General procedure: To a solution of m-CPBA(1.2 mmol) and CuBr2 (0.1 mmol) in dry 1,4-dioxane (10 mL) was addeddropwise a solution of compound 1 (1mmol). The reaction mixture was stirred at the designated temperature until theTLC indicated the consumption of the starting martial compound 1. After the reaction was completed,the reaction mixture was allowed to cool to room temperature, and EtOAc (20 mL)was added. The resulting mixture was washed with saturated aqueous Na2S2O3(10mL) and saturated aqueousNa2CO3 (10 mL). The organic layer was dried overanhydrous Na2SO4, filtered, and removed under reducedpressure. The residue was purified by flash column chromatography on silica gelto give the desired products.
Reference: [1] Tetrahedron Letters, 2015, vol. 56, # 31, p. 4634 - 4637
  • 4
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YieldReaction ConditionsOperation in experiment
60% at 80℃; Example 18: Methyl 4-fluorophenylacetate 1 (Z = COOCH3, F = 4-F, X = H)Under inert atmosphere 0.6 g methyl 2- (2,35- difluorophenyl) -2-chloroacetate is dissolved in 20 mL methanol, 1 g sodium dithionite is added and the mixture is heated to 80° C. Once the conversion is completed, the mixture is cooled to room temperature, concentrated in vacuum, taken up again with toluene, and washed with an aqueous sodium carbonate solution and then with water. The organic layer is concentrated in vacuum, yielding 0.3 g of product (60percent) with 90percent purity GC (Apercent) . MS m/e: 168 (M+) .
Reference: [1] Patent: WO2008/78350, 2008, A2, . Location in patent: Page/Page column 23
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Reference: [1] Journal of Organic Chemistry, 1996, vol. 61, # 5, p. 1748 - 1755
  • 6
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  • [ 201230-82-2 ]
  • [ 140-75-0 ]
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Reference: [1] ACS Catalysis, 2018, vol. 8, # 1, p. 738 - 741
  • 7
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Reference: [1] ACS Catalysis, 2018, vol. 8, # 1, p. 738 - 741
  • 8
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Reference: [1] Journal of Organic Chemistry, 2013, vol. 78, # 8, p. 4123 - 4131
  • 9
  • [ 67-56-1 ]
  • [ 459-56-3 ]
  • [ 201230-82-2 ]
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Reference: [1] Green Chemistry, 2018, vol. 20, # 5, p. 969 - 972
  • 10
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Reference: [1] Tetrahedron Letters, 2007, vol. 48, # 17, p. 3003 - 3007
  • 11
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Reference: [1] Journal of Organic Chemistry, 2009, vol. 74, # 1, p. 445 - 447
  • 12
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Reference: [1] Patent: US2007/15923, 2007, A1, . Location in patent: Page/Page column 7; 8
[2] Patent: WO2008/54690, 2008, A2, . Location in patent: Page/Page column 13-14
  • 13
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Reference: [1] Indian Journal of Chemistry - Section B Organic Chemistry Including Medicinal Chemistry, 1990, vol. 29, # 4, p. 304 - 309
[2] Indian Journal of Chemistry - Section B Organic Chemistry Including Medicinal Chemistry, 1990, vol. 29, # 4, p. 304 - 309
  • 14
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Reference: [1] Tetrahedron Letters, 2015, vol. 56, # 31, p. 4634 - 4637
  • 15
  • [ 18107-18-1 ]
  • [ 405-50-5 ]
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Reference: [1] Bioorganic and Medicinal Chemistry Letters, 2003, vol. 13, # 1, p. 119 - 123
  • 16
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YieldReaction ConditionsOperation in experiment
97% With hydrazine In methanol at 60℃; for 2 h; Heating / reflux Neat anh. hydrazine 20 mL was added to a slurry of (4-fluorophenyl) acetic acid methyl ester (Acros Organics USA, Morris Plains, NJ, 25.66g, 152.5 MMOL) in MEOH (120ML) and the mixture was heated to 60 °C with reflux condenser under nitrogen for 2 hrs. Cooled to R. T., evaporated to dryness (R. T. to 60 °C, 100 Torr to 7 Torr). The solid residue was RE- crystallized from 1-propanol, 100mL (reflux to R. T., overnight). The cryst. product was collected by filtration, washed with 1-propanol and dried on high vacuum. [1St fraction]. Evaporating the supernatants to dryness on high vacuum, the obtained solid residue was dried on high vacuum overnight. The residue was then RE-CRYSTAIIIZED from benzene. (reflux to R. T. , overnight) The precipitated product was collected by filtration, washed with a mixture benzene-hexane (1: 1), then with hexane. Dried on high vacuum. [2 ID fraction]. Combined yield : 24. 855G of a white cryst. flakes (97percent). H-NMR (DMSO-D6, 400 MHz) : 9.194 (br s, 1 H), 7.272 (m, 2H), 7.107 (m, 2H), 4.202 (br d, J=4.3 Hz, 2H), 3.329 (s, 2H) ;'9F-NMR (DMSO-D6, 376.5 MHz):-116. 96 (m, 1 F).
77% With hydrazine hydrate In ethanol at 40℃; General procedure: Various methyl benzoate 8A-V (1.0 equiv) reacted with hydrazine hydrate (excess amount) in anhydrous ethanol. The reaction was stirred at 40 °C for overnight. The ethanol was removed under reduced pressure. The products were purified by recrystallization, which were washed with ethyl ether. The products were obtained as white solid.
Reference: [1] Patent: WO2005/10005, 2005, A1, . Location in patent: Page/Page column 29-30
[2] European Journal of Medicinal Chemistry, 2016, vol. 120, p. 202 - 216
[3] Bulletin of the Korean Chemical Society, 2012, vol. 33, # 12, p. 3943 - 3949
[4] Bioorganic and Medicinal Chemistry Letters, 2014, vol. 24, # 7, p. 1677 - 1680
[5] Bioorganic and Medicinal Chemistry Letters, 2015, vol. 25, # 3, p. 481 - 484
[6] Journal of Chemistry, 2017, vol. 2017,
[7] Bioorganic and Medicinal Chemistry Letters, 2018, vol. 28, # 14, p. 2369 - 2374
  • 17
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[2] Journal of Organic Chemistry, 2003, vol. 68, # 19, p. 7234 - 7242
[3] Patent: WO2013/87579, 2013, A1,
[4] Patent: WO2014/9219, 2014, A1,
[5] Patent: WO2014/195276, 2014, A1,
[6] Patent: WO2014/198594, 2014, A1,
[7] Patent: WO2014/198647, 2014, A2,
[8] Patent: US2015/148542, 2015, A1,
[9] Patent: WO2016/91825, 2016, A1,
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