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Chemical Structure| 1590-25-6
Chemical Structure| 1590-25-6
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Product Details of [ 1590-25-6 ]

CAS No. :1590-25-6 MDL No. :MFCD00126480
Formula : C12H9BrO Boiling Point : -
Linear Structure Formula :- InChI Key :UZDOTHVVSQOCJO-UHFFFAOYSA-N
M.W : 249.10 Pubchem ID :12433082
Synonyms :

Calculated chemistry of [ 1590-25-6 ]

Physicochemical Properties

Num. heavy atoms : 14
Num. arom. heavy atoms : 10
Fraction Csp3 : 0.08
Num. rotatable bonds : 1
Num. H-bond acceptors : 1.0
Num. H-bond donors : 0.0
Molar Refractivity : 61.84
TPSA : 17.07 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : Yes
P-gp substrate : No
CYP1A2 inhibitor : Yes
CYP2C19 inhibitor : Yes
CYP2C9 inhibitor : No
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -5.3 cm/s

Lipophilicity

Log Po/w (iLOGP) : 2.42
Log Po/w (XLOGP3) : 3.55
Log Po/w (WLOGP) : 3.8
Log Po/w (MLOGP) : 3.44
Log Po/w (SILICOS-IT) : 3.98
Consensus Log Po/w : 3.44

Druglikeness

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

Water Solubility

Log S (ESOL) : -4.08
Solubility : 0.0206 mg/ml ; 0.0000825 mol/l
Class : Moderately soluble
Log S (Ali) : -3.59
Solubility : 0.0635 mg/ml ; 0.000255 mol/l
Class : Soluble
Log S (SILICOS-IT) : -5.27
Solubility : 0.00135 mg/ml ; 0.00000542 mol/l
Class : Moderately soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 2.0
Synthetic accessibility : 1.07

Safety of [ 1590-25-6 ]

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

Application In Synthesis of [ 1590-25-6 ]

* 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.

  • Upstream synthesis route of [ 1590-25-6 ]
  • Downstream synthetic route of [ 1590-25-6 ]

[ 1590-25-6 ] Synthesis Path-Upstream   1~16

  • 1
  • [ 1590-25-6 ]
  • [ 50637-83-7 ]
YieldReaction ConditionsOperation in experiment
76%
Stage #1: for 0.166667 h;
Stage #2: for 4 h;
Intermediate 4: 2-Bromo-l-(6-bromo-2-naphthalenyl)ethanone (Scheme 1); To the l-(6-bromo-2-naphthalenyl)ethanone (lg, 4.01 mmol) dissolved in acetic acid (5ml) was added pyridinium tribromide (1.28 g, 4.01 mmol) and stirred for lOmin. HBr (33percent in acetic acid, 1.321 ml, 8.03 mmol) was added slowly and the solution was stirred for 4h. Yellow precipitation was noticed. The reaction mixture was quenched by adding cold sat NaHC03 solution and the precipitate formed was filtered and washed with water and dried.Yield : 76.0percent'H NMR (400 MHz, CHLOROFORM-d) δ ppm 8.50 (s, 1 H), 8.03 - 8.13 (m, 2 H), 7.79 - 7.91 (m, 2 H), 7.67(dd, J=8.8, 1.5 Hz, 1 H), 4.57 (s, 2 H).
73% at 20℃; Bromine (3.32 g, 1.07 ml, 20.8 mmol) was added to a heated solution of 1-(6-bromonaphthalen-2-yl)ethanone (5.18 g, 20.8 mmol) in acetic acid (100 mL).
Left to cool to rt overnight.
The precipitate was filtered, washed with Et2O and dried under vacuum to give 2-bromo-1-(6-bromonaphthalen-2-yl)ethanone (5.02 g, 73percent).
70% With copper bromide In chloroform; ethyl acetate at 10℃; Reflux S2 (249.1 mg, 1.0 mmol) andCopper bromide (223.4 mg, 1.5 mmol)Add 25mL dried egg-shaped bottle,Add 5mL ethyl acetate and 5mL chloroform solution at room temperature to make the raw material completely dissolved,Then refluxed overnight. TLC tracking until the conversion of raw materials is completed,Remove the solvent after stopping heating to room temperature.Ethyl acetate was added to the bottle to dissolve it, followed by saturated brine and waterThe combined organic phases were dried over anhydrous sodium sulfate.After concentration under reduced pressure, the crude product was purified by column chromatography (petroleum ether → petroleum ether:Ethyl acetate = 20: 1) to give S3 (230.1 mg, 70percent yield) as a white solid.
67% With bromine In dichloromethane at 15℃; Step A - Synthesis of compound Int-39b Compound Int-39a (6 g, 24.09 mmol) in CH2C12 (80 mL) was treated dropwise with Br2 (1.253 mL, 24.33 mmol). The mixture was allowed to stir for about 15 hours then concentrated in vacuo. The residue obtained was recrystalhzed from THF to provide compound Int-39b, which was dried in vacuo (5.3g; 67percent).
37.82% at 20℃; for 1 h; Compound AA_072-2 (3.5 g, 14.06 mmol) was dissolved in acetic acid (30 mL), liquid bromine (2.2 g, 14.06 mmol) was dripped slowly. After dripping, the reaction mixture was stirred at room temperature for 1 h. After the reaction was complete as detected by TLC, H2O (80 mL) was added. The reaction mixture was filtrated and the solid was collected to deliver the target compound AA_072-3 (white solid, 1.74 g, yield 37.82percent). The product was directly used for the next step without purification. 1H NMR (CDCl3, 400 MHz): δ 8.12-8.05 (m, 2H), 7.88-7.85 (m, 3H), 7.83-7.68 (m, 1H), 4.56 (s, 2H).
7 g With bromine In 1,4-dioxane; dichloromethane at 10℃; for 2 h; To a solution of bromide B-la (5.0 g, 20.07 mmol) in DCM (150 mL) was added B (0.827 mL, 16.06 mmol) in dioxane (50 mL) over 10 minutes at 10 °C and the reaction mixture was stirred at 10 °C for 2 h. The reaction mixture was quenched with 10percent aHC03and extracted with DCM. The organic layer was dried over Na2S04and concentrated to obtain crude dibromide B-lb (7.0 g) as a yellow solid. NMR (CDC13), δ = 7.26 ppm, 400 MHz): δ 8.48 (s, 1 H), 8.07- 8.04 (m, 2 H), 7.85 (d, J = 8.8, 1 H), 7.84 (d, J = 8.8, 1 H), 7.66 (dd, J = 8.8, 2.0, 1 H), 4.55 (s, 2 H).

Reference: [1] Patent: WO2011/91446, 2011, A1, . Location in patent: Page/Page column 7; 11
[2] Patent: US2012/230951, 2012, A1, . Location in patent: Page/Page column 85
[3] Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 2011, vol. 50, # 4, p. 593 - 604
[4] Patent: CN107286150, 2017, A, . Location in patent: Paragraph 0132; 0133; 0134; 0135
[5] Patent: WO2013/39878, 2013, A1, . Location in patent: Page/Page column 109; 110
[6] Patent: US2017/253614, 2017, A1, . Location in patent: Paragraph 0574; 0576
[7] Justus Liebigs Annalen der Chemie, 1973, p. 1112 - 1140
[8] Journal of Medicinal Chemistry, 1981, vol. 24, # 1, p. 67 - 74
[9] Indian Journal of Chemistry, Section A: Inorganic, Physical, Theoretical & Analytical, 1984, vol. 23, # 12, p. 1008 - 1010
[10] Indian Journal of Chemistry, Section A: Inorganic, Physical, Theoretical & Analytical, 1984, vol. 23, # 12, p. 1008 - 1010
[11] Patent: US2011/64695, 2011, A1, . Location in patent: Page/Page column 94
[12] Patent: US2011/64697, 2011, A1, . Location in patent: Page/Page column 85
[13] Patent: US2011/64698, 2011, A1, . Location in patent: Page/Page column 87
[14] Patent: WO2011/54834, 2011, A1,
[15] Patent: WO2012/13643, 2012, A1, . Location in patent: Page/Page column 26
[16] Patent: US2012/219594, 2012, A1,
[17] Patent: US2015/23913, 2015, A1, . Location in patent: Paragraph 0995-0996
[18] Patent: WO2015/5901, 2015, A1, . Location in patent: Page/Page column 370
[19] Patent: US9127021, 2015, B2, . Location in patent: Page/Page column 153
[20] Patent: WO2010/99527, 2010, A1, . Location in patent: Page/Page column 118
  • 2
  • [ 861880-64-0 ]
  • [ 75-16-1 ]
  • [ 1590-25-6 ]
YieldReaction ConditionsOperation in experiment
99%
Stage #1: at 10 - 15℃; for 1.5 h; Inert atmosphere
Stage #2: With hydrogenchloride In tetrahydrofuran; 2-methyltetrahydrofuran; waterCooling with ice
6-bromo-N-methoxy-N-methyl-2-naphthamide (82.9 g, 282 mmol, 1 equiv.) was dissolved in tetrahydrofurane (600 mL) in a 4-neck flask under nitrogen. The reaction mixture was cooled in an ice bath and methyl magnesium bromide (3.2 M in methyl- tetrahydrofurane, 197 mL, 2.2 equiv.) was added drop wise during 1 hour, while maintaining the temperature of the reaction mixture between 10-15°C. The reaction mixture was stirred 30 minutes further in an ice bath. Aqueous hydrochloric acid (2 M, 100 mL) was then carefully added drop wise while cooling on an ice bath. The organic solvent was evaporated and the precipitated product extracted with dichloromethane (500 mL). The solution was dried over sodium sulphate, filtered and concentrated. The solid residue was dried in vacuum at 40°C yielding l-(6-bromonaphthalen-2-yl)- ethanone (70.6 g, 99 percent).
76%
Stage #1: at 0 - 20℃; for 14 h;
Stage #2: With hydrogenchloride; water In tetrahydrofuran for 0.166667 h;
Intermediate 3: l-(6-Bromo-2-naphthalenyl)ethanone (Scheme 1); Methylmagnesium bromide (1.133 mL, 3.40 mmol), was added to 6-bromo-N- methyl-N-(methyloxy)-2-naphthalenecarboxamide (500mg, 1.70 mmol) in THF at 0°C. Stirring continued for 2h at 0°C and allowed to reach T and stirred for additional 12h. Aqueous 0.5 M HCl (ImL) and 0.5mL H20 (1 mL) was added, stirred for lOmin and the light yellow color THF layer was decanted. The solid layer was washed with ethyl acetate. After evaporation of the solvent, the material was subjected to silica gel chromatography using 50percent ethyl acetate to 100percent in hexane to provide pure compound. Yield : 76.0percent.'H MR (400 MHz, CHLOROFORM-d) δ ppm 8.39 - 8.47 (m, 1 H), 8.02 - 8.12 (m, 2 H), 7.79 - 7.90 (m, 2 H), 7.60 - 7.69 (m, 1 H), 2.74 (s, 3 H);ES LC-MS m/z = 250.1 (M+H)+;
40.4% at 0 - 20℃; for 2 h; At room temperature, 6-bromo-2-naphthoic acid (AA_072-1, 10 g, 39.83 mmol), N,O-dimethyl hydroxylamine hydrochloride (5.05 g, 51.76 mmol) and DIPEA (15.44 g, 119.49 mmol) were dissolved in DMF (100 mL), HATU (23 g, 59.7 mmol) was added. The reaction mixture was stirred at room temperature for 4 h. After the reaction was complete as detected by TLC, methyl tert-butyl ether (300 mL) was added and the reaction mixture was washed with H2O and saturated brines. The organic phase was dried over anhydrous sodium sulfate. After filtration, the filtrate was concentrated by a rotary evaporator to remove the solvent thereby giving Weinreb amide (5.8 g, yield 90percent). The product was directly used for the next step without purification. The Weinreb amide (5.8 g, 35.9 mmol) was dissolved in THF (25 mL), cooled to 0° C., a solution of methyl magnesium bromide in ethyl ether (3 mol/L, 7.9 mL, 23.7 mmol) was dripped slowly. After dripping, the reaction mixture was stirred at room temperature for 2 h. After the reaction was complete as detected by TLC, the reaction was quenched with saturated ammonium chloride solution (50 mL) and extracted with ethyl acetate (50 mL×3). The organic phases were combined and dried over anhydrous sodium sulfate. After filtration, the filtrate was concentrated by a rotary evaporator to remove the solvent thereby delivering the target compound AA_072-2 (white solid, 4 g, yield: 40.4percent). The product was directly used for the next step without purification. 1H NMR (CDCl3, 400 MHz): δ 8.43 (s, 1H), 8.06 7.85-7.80 (m, 2H), 7.85-7.80 (m, 2H), 7.65 (d, J=2.0 Hz, 1H).
Reference: [1] Patent: WO2011/54834, 2011, A1, . Location in patent: Page/Page column 39
[2] Patent: WO2011/91446, 2011, A1, . Location in patent: Page/Page column 11
[3] Patent: US2017/253614, 2017, A1, . Location in patent: Paragraph 0574; 0575
[4] Patent: US2011/64695, 2011, A1, . Location in patent: Page/Page column 94
[5] Patent: US2011/64697, 2011, A1, . Location in patent: Page/Page column 85
[6] Patent: US2011/64698, 2011, A1, . Location in patent: Page/Page column 87
[7] Patent: US9127021, 2015, B2, . Location in patent: Page/Page column 153
[8] Patent: WO2010/99527, 2010, A1, . Location in patent: Page/Page column 118
  • 3
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YieldReaction ConditionsOperation in experiment
49% With aluminum (III) chloride In nitrobenzene at 100℃; for 4 h; 2-bromo-naphthalene (0.5 g, 2.41 mmol), AlCl3 (0.338 g, 2.53 mmol) and AcCl (0.172 mL, 2.41 mmol) weredissolved in 3.4 mL of nitrobenzene, and stirred at 100°C for 4 hours under reflux. After addition of water, the reactionsolution extracted with EtOAc. The organic layer was separated, dried with MgSO4 and purified by column chromatographyto obtain the title compound (0.3 g, 49percent).1H-NMR (CDCl3) δ 8.43 (1H, s), 8.06 (2H, m), 7.82 (2H, t), 7.63 (1H, m), 2.72 (3H, s).
42%
Stage #1: With aluminum (III) chloride In nitrobenzene at 100℃; for 4 h;
Stage #2: With water In nitrobenzene
A mixture of 2-bromonaphthalene (950 g, 4589 mmol), acetyl chloride (260 mL,4589 mmol), nitrobenzene (6000 mL) and aluminum chloride (642.2 g, 4818 mmol) was stirred for 4 hours at 100°C. The mixture was poured onto ice water, the resulting slurry was filtrated and the organic phase separated from the filtrate. The organic phase was washed with water (2000 mL), dried over Na2S04 and filtrated. The solvent was removed by distillation. The residue was re-crystallized from a solution of hexane: ethyl acetate (10: 1) resulting in l-(6-bromonaphthalen-2-yl)ethanone (480 g, 42percent yield).
37% With aluminum (III) chloride In nitrobenzene at 100℃; for 4 h; Into a four-necked flask of 500 ml,Then, 41.4 g of 2-bromonaphthalene, 15.7 g of acetyl chloride, 28 g of aluminum chloride and 250 mℓ of nitrobenzene were charged and stirred at 100 ° C. for 4 hours.Then, upon reaching below cooling to 30 ° C., the reaction mixture was poured into ice water, was removed and the precipitated precipitate was filtered off.The filtrate after washing twice with water 100 ml, dried over anhydrous magnesium sulfate, the solvent was removed under reduced pressure. The residue is recrystallized from hexane to give 18.42g of 2-bromo-6-acetyl naphthalene. (Yield 37.0percent)1H-NMR (400 MHz, CDCl3): δH 2.71 (s, 3H), 7.63 (dd, 1H), 7.80 (d, 1H), 7.82 (d, 2H), 8.05 (M, 2 H), 8.42 (s, 1 H)
36%
Stage #1: With aluminum (III) chloride In nitrobenzene at 100℃; for 4 h;
Stage #2: With water In nitrobenzeneCooling with ice
Alternative for preparation of l-(6-bromonaphthalen-2-yl)ethanone; A mixture of 2-bromonaphthalene (41.4 g, 200 mmol), acetyl chloride (11.3 mL, 160 mmol), nitrobenzene (250 mL) and A1C13 (28g, 210 mmol) was stirred for 4 hours at 100°C (oil bath temperature). The resulting reaction mixture was cooled, poured onto ice /water (100 mL) and filtered. The filtrate was washed with water (100 mL). The solvent (nitrobenzene) was removed by distillation. The resulting residue was crystallized from hexane to afford 18 g of desired product (36percent yield).l-(6-bromonaphthalen-2-yl)ethanone: 1H NMR (400 MHz, ACETONITRILE- 3) δ ppm 2.66 (s, 3 H) 7.66 (dd, J=8.8, 2.0 Hz, 1 H) 7.86 (d, J=8.8 Hz, 1 H) 7.94 (d, J=8.8 Hz, 1 H) 8.02 (dd, J=8.8, 1.8 Hz, 1 H) 8.13 (d, J=2.0 Hz, 1 H) 8.53 (d, J=1.8 Hz, 1 H).
11 g With aluminum (III) chloride In nitrobenzene at 10 - 40℃; for 18 h; To a solution of 2-bromonaphthalene (25 g, 121 mmol) and AlCl3(19.32 g, 145 mmol) in nitrobenzene (227 mL) was added AcCl (10.78 mL, 152 mmol) at 10° C. The reaction mixture was heated to 40° C. for 18 h. Then the reaction mixture was cooled to rt and poured into ice containing con. HCl (400 mL). The reaction mixture was extracted with EtOAc and washed with 1.5 N HCl solution, brine, dried over Na2SO4and concentrated. The crude was purified by column chromatography (Silica gel 60-120, 3-5percent EtOAc/petroleum ether) to obtain bromide B-1a (11 g) as light brown solid.1H NMR (CDCl3), δ=7.26 ppm, 400 MHz): δ 8.43 (s, 1H), 8.08-8.04 (m, 2H), 7.84 (d, J=8.8, 1H), 7.81 (d, J=8.8, 1H), 7.64 (dd, J=8.8, 2.0, 1H), 2.72 (s, 3H).
11 g With aluminum (III) chloride In nitrobenzene at 10 - 40℃; for 10 h; To a solution of 2-bromonaphthalene (25 g, 121 mmol) and AICI3 (19.32 g,145 mmol) in nitrobenzene (227 mL) was added AcCl (10.78 mL, 152 mmol) at 10 °C. The reaction mixture was heated to 40 °C for 18 h. Then the reaction mixture was cooled to rt and poured into ice containing con. HCl (400 mL). The reaction mixture was extracted with EtOAc and washed with 1.5 N HCl solution, brine, dried over Na2S04and concentrated. The crude was purified by column chromatography (Silica gel 60-120, 3-5percent EtOAc/petroleum ether) to obtain bromide B-la (11 g) as light brown solid.XH NMR (CDC13), δ = 7.26 ppm, 400 MHz): δ 8.43 (s, 1 H), 8.08- 8.04 (m, 2 H), 7.84 (d, J = 8.8, 1 H), 7.81 (d, J = 8.8, 1 H), 7.64 (dd, J = 8.8, 2.0, 1 H), 2.72 (s, 3 H).

Reference: [1] Patent: EP3239143, 2017, A2, . Location in patent: Paragraph 0306
[2] Patent: WO2012/13643, 2012, A1, . Location in patent: Page/Page column 25-26
[3] Patent: JP2017/39655, 2017, A, . Location in patent: Paragraph 0044
[4] Patent: WO2011/54834, 2011, A1, . Location in patent: Page/Page column 39
[5] Chemical Communications, 2015, vol. 51, # 38, p. 8153 - 8156
[6] Angewandte Chemie - International Edition, 2016, vol. 55, # 26, p. 7530 - 7533[7] Angew. Chem., 2016, vol. 128, # 26, p. 7656 - 7659,4
[8] Chemische Berichte, 1891, vol. 24, p. 550
[9] Bulletin of the Chemical Society of Japan, 1975, vol. 48, p. 3356 - 3366
[10] Patent: US5877207, 1999, A,
[11] Patent: US5958954, 1999, A,
[12] Patent: US4766127, 1988, A,
[13] Patent: US2012/219594, 2012, A1,
[14] Patent: US2015/23913, 2015, A1, . Location in patent: Paragraph 0993-0994
[15] Patent: WO2015/5901, 2015, A1, . Location in patent: Page/Page column 369
  • 4
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YieldReaction ConditionsOperation in experiment
99% With hydrogenchloride In tetrahydrofuran; 2-methyltetrahydrofuran; methylmagnesium bromide Step 3
6-bromo-N-methoxy-N-methyl-2-naphthamide (82.9 g, 282 mmol, 1 equiv.) was dissolved in tetrahydrofurane (600 mL) in a 4-neck flask under nitrogen.
The reaction mixture was cooled in an ice bath and methyl magnesium bromide (3.2 M in methyl-tetrahydrofurane, 197 mL, 2.2 equiv.) was added drop wise during 1 hour, while maintaining the temperature of the reaction mixture between 10-15° C.
The reaction mixture was stirred 30 minutes further in an ice bath.
Aqueous hydrochloric acid (2 M, 100 mL) was then carefully added drop wise while cooling on an ice bath.
The organic solvent was evaporated and the precipitated product extracted with dichloromethane (500 mL).
The solution was dried over sodium sulphate, filtered and concentrated.
The solid residue was dried in vacuum at 40° C. yielding 1-(6-bromonaphthalen-2-yl)-ethanone (70.6 g, 99percent).
Alternative for Preparation of 1-(6-bromonaphthalen-2-yl)ethanone
Reference: [1] Patent: US2012/219594, 2012, A1,
  • 5
  • [ 201230-82-2 ]
  • [ 594-27-4 ]
  • [ 151600-02-1 ]
  • [ 1590-25-6 ]
Reference: [1] Tetrahedron Letters, 2001, vol. 42, # 2, p. 265 - 266
  • 6
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  • [ 676-58-4 ]
  • [ 1590-25-6 ]
Reference: [1] Patent: CN107286150, 2017, A, . Location in patent: Paragraph 0128; 0129; 0130; 0131
  • 7
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Reference: [1] Patent: WO2011/54834, 2011, A1,
[2] Patent: US2012/219594, 2012, A1,
[3] Patent: WO2011/91446, 2011, A1,
[4] Patent: CN107286150, 2017, A,
[5] Patent: US2017/253614, 2017, A1,
  • 8
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Reference: [1] Patent: WO2011/54834, 2011, A1,
[2] Patent: US2012/219594, 2012, A1,
[3] Patent: WO2011/91446, 2011, A1,
[4] Patent: CN107286150, 2017, A,
  • 9
  • [ 111-34-2 ]
  • [ 151600-02-1 ]
  • [ 1590-25-6 ]
Reference: [1] Journal of Organic Chemistry, 2011, vol. 76, # 15, p. 6367 - 6371
  • 10
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Reference: [1] Journal of Organic Chemistry, 2011, vol. 76, # 15, p. 6367 - 6371
  • 11
  • [ 75-15-0 ]
  • [ 7446-70-0 ]
  • [ 580-13-2 ]
  • [ 75-36-5 ]
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Reference: [1] Journal of the American Chemical Society, 1943, vol. 65, p. 239,241
[2] Journal of Organic Chemistry, 1948, vol. 13, p. 164,165
[3] Journal of Organic Chemistry, 1946, vol. 11, p. 163
[4] Bulletin de l'Academie Polonaise des Sciences, Serie des Sciences Chimiques, 1931, vol. <A>, p. 59,65
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Reference: [1] Journal of the American Chemical Society, 1943, vol. 65, p. 239,241
[2] Journal of Organic Chemistry, 1948, vol. 13, p. 164,165
[3] Journal of Organic Chemistry, 1946, vol. 11, p. 163
[4] Bulletin de l'Academie Polonaise des Sciences, Serie des Sciences Chimiques, 1931, vol. <A>, p. 59,65
  • 13
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  • [ 5773-80-8 ]
YieldReaction ConditionsOperation in experiment
70% With sodium hypochlorite; sodium hydroxide In 1,4-dioxane; water at 70℃; for 4 h; 1-(6-bromo-naphthalen-2-yl)ethaneone (0.22 g, 0.88 mmol) obtained in Preparation Example 100 was dissolvedin 3 mL of 1,4-dioxane. NaOH (0.353 g, 8.8 mmol) dissolved in 3 mL of water and 9-11percent NaOCl solution (1.67mL, 2.64 mmol) were added thereto, and the mixture was heated to 70°C and stirred for 4 hours. After addition of NaHSO3aqueous solution and water, the reaction solution was extracted with ether. 1N HCl was added thereto, and the organiclayer was separated, dried with MgSO4 and purified by column chromatography to obtain the title compound (0.156 g,70percent).1H-NMR (CDCl3) δ 8.56 (1H, s), 8.05 (2H, m), 7.79 (2H, m), 7.58 (1H, m).
88% With sodium hydroxide; sodium hypochlorite In 1,4-dioxane; water 6-bromo-2-naphthalenecarboxylic acid (Compound M)
To a solution of sodium hypochlorite (62 ml, 5.25percent in water (w/w), 3.6 g, 48.18 mmol) and sodium hydroxide (6.4 g, 160.6 mmol) in 50 ml of water was added a solution of 2-acetyl-6-bromonaphthalene (Compound L) 4 g, (16.06 mmol) in 50 ml of 1,4-dioxane.
The yellow solution was heated to 70° C. in an oil bath for 2 hours, cooled to ambient temperature, and extracted with ethyl ether (2*50 ml).
The aqueous layers were diluted with NaHSO3 solution (until KI indicator solution remained colorless) and then acidified (pH <2) with 1N sulfuric acid to give a white precipitate.
The mixture was extracted with ethyl ether, and the combined organic phase washed with saturated aqueous NaCl, dried (MgSO4) and concentrated to give 3.54 g (88percent) of the title compound as a solid. 1H NMR (DMSO-d6): δ 8.63 (1H, br s), 8.32 (1H, d, J=2.0 Hz), 8.10 (1H, d, J=8.8 Hz), 8.00-8.05 (2H, m), 7.74 (1H, dd, J=2.0, 8.8 Hz).
88% With sodium hydroxide; sodium hypochlorite In 1,4-dioxane; sulfuric acid; water 6-bromo-2-naphthalenecarboxylic acid (Compound M)
To a solution of sodium hypochlorite (62 ml, 5.25percent in water (w/w), 3.6 g, 48.18 mmol) and sodium hydroxide (6.4 g, 160.6 mmol) in 50 ml of water was added a solution of 2-acetyl-6-bromonaphthalene (Compound L) 4 g, (16.06 mmol) in 50 ml of 1,4-dioxane.
The yellow solution was heated to 70° C. in an oil bath for 2 hours, cooled to ambient temperature, and extracted with ethyl ether (2*50 ml).
The aqueous layers were diluted with NaHSO3 solution (until KI indicator solution remained colorless) and then acidified (pH<2) with IN sulfuric acid to give a white precipitate.
The mixture was extracted with ethyl ether, and the combined organic phase washed with saturated aqueous NaCl, dried (MgSO4) and concentrated to give 3.54 g (88percent) of the title compound as a solid. 1H NMR (DMSO-d6): δ 8.63 (1H, br s), 8.32 (1H, d, J=2.0 Hz), 8.10 (1H, d, J=8.8 Hz), 8.00-8.05 (2H, m), 7.74 (1H, dd, J=2.0, 8.8 Hz).
Reference: [1] Patent: EP3239143, 2017, A2, . Location in patent: Paragraph 0306
[2] Patent: US5877207, 1999, A,
[3] Patent: US5958954, 1999, A,
  • 14
  • [ 580-13-2 ]
  • [ 1590-25-6 ]
  • [ 75-36-5 ]
  • [ 5773-80-8 ]
Reference: [1] Patent: US4454341, 1984, A,
  • 15
  • [ 1590-25-6 ]
  • [ 5773-80-8 ]
Reference: [1] Patent: US4447452, 1984, A,
  • 16
  • [ 1590-25-6 ]
  • [ 5773-80-8 ]
  • [ 32405-50-8 ]
Reference: [1] Indian Journal of Chemistry, Section A: Inorganic, Physical, Theoretical & Analytical, 1980, vol. 19, # 7, p. 646 - 649
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