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Product Details of [ 23351-91-9 ]

CAS No. :23351-91-9 MDL No. :MFCD00152019
Formula : C8H5BrO4 Boiling Point : -
Linear Structure Formula :- InChI Key :JATKASGNRMGFSW-UHFFFAOYSA-N
M.W : 245.03 Pubchem ID :90073
Synonyms :

Calculated chemistry of [ 23351-91-9 ]

Physicochemical Properties

Num. heavy atoms : 13
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.0
Num. rotatable bonds : 2
Num. H-bond acceptors : 4.0
Num. H-bond donors : 2.0
Molar Refractivity : 48.06
TPSA : 74.6 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : Yes
P-gp substrate : No
CYP1A2 inhibitor : No
CYP2C19 inhibitor : No
CYP2C9 inhibitor : No
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -6.61 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.04
Log Po/w (XLOGP3) : 1.67
Log Po/w (WLOGP) : 1.85
Log Po/w (MLOGP) : 1.93
Log Po/w (SILICOS-IT) : 1.3
Consensus Log Po/w : 1.56

Druglikeness

Lipinski : 0.0
Ghose : None
Veber : 0.0
Egan : 0.0
Muegge : 0.0
Bioavailability Score : 0.56

Water Solubility

Log S (ESOL) : -2.62
Solubility : 0.587 mg/ml ; 0.00239 mol/l
Class : Soluble
Log S (Ali) : -2.85
Solubility : 0.346 mg/ml ; 0.00141 mol/l
Class : Soluble
Log S (SILICOS-IT) : -2.0
Solubility : 2.43 mg/ml ; 0.00993 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.54

Safety of [ 23351-91-9 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P280-P305+P351+P338 UN#:N/A
Hazard Statements:H317-H319 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 23351-91-9 ]

* 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 [ 23351-91-9 ]
  • Downstream synthetic route of [ 23351-91-9 ]

[ 23351-91-9 ] Synthesis Path-Upstream   1~22

  • 1
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YieldReaction ConditionsOperation in experiment
85% With dimethylsulfide borane complex In tetrahydrofuran at 0 - 20℃; Inert atmosphere 5-bromoisophtalic acid (25.0 gram, 0.102 mol, 1 equiv) was dissolved in dry THF (500 mL) at 0 °C under argon atmosphere. 10M Borane dimethylsulfide complex (50 mL, 0.50 mmol, 5 equiv) was added and the mixture was stirred at room temperature overnight. H20 (1000 mL) was added carefully to the mixture followed by addition of EtOAc (1000 mL). After separation of the layers, the organic layer was washed with H20 (3 >< 750 mL) and brine (1000 mL). The organic layer was dried over MgSO4, filtered and (0296) concentrated in racuo yielding alcohol 7 as a white powder in 85percent yield with no need for further purification. 1H NMR (400 MHz, DMSO) 8 7.36 (s, 2H), 7.25 (s, 1H), 5.30 (t, 2H), 4.48 (d, 4H). 13C NMR (400 MHZ, DMSO) 6 145.2, 127.1, 123.1, 121.3, 62.1. IR V 3210, 2851, 1602, 1419 cm-1. HRMS (FD+) m/z caIcuIated for C8H9BrOz 215.9786, found 215.9798. Spectral data in agreement with reported data (Wytko and Weiss, 1994).
81% With sodium tetrahydroborate; boron trifluoride diethyl etherate In tetrahydrofuran at 20℃; for 2 h; Inert atmosphere; Cooling with ice A solution of 5-bromoisophthalic acid (5 g, 20.4 mmol) in tetrahydrofuran (80 ml) was added to a solution of sodium borohydride (2.76 g, 73.0 mmol) in tetrahydrofuran (20 ml) under an argon atmosphere and ice cooling, followed by stirring. Boron trifluoride diethyl ether complex (7.6 ml, 60.9 mmol) was added over 1 hour while cooling on ice, and the temperature was returned to room temperature and stirred for 1 hour. A 0.5 mol/l sodium hydroxide aqueous solution (40 ml) was added to the reaction solution, and the mixture was extracted with ethyl acetate. The aqueous layer was further extracted twice with ethyl acetate, the organic layer was washed with saturated brine, and dried over anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure and the residue was purified on a column to give (5-bromo-1,3-phenylene) dimethanol (3.60 g, 81percent) as a white solid.
Reference: [1] Tetrahedron Letters, 2000, vol. 41, # 7, p. 1015 - 1018
[2] Journal of Medicinal Chemistry, 2013, vol. 56, # 7, p. 3024 - 3032
[3] Angewandte Chemie - International Edition, 2018, vol. 57, # 2, p. 501 - 505[4] Angew. Chem., 2018, vol. 130, p. 510 - 514,5
[5] Patent: WO2018/106112, 2018, A1, . Location in patent: Page/Page column 76; 77; 82
[6] Patent: JP2015/224231, 2015, A, . Location in patent: Paragraph 0070
[7] New Journal of Chemistry, 2009, vol. 33, # 2, p. 345 - 357
[8] Tetrahedron Letters, 1991, vol. 32, # 49, p. 7261 - 7264
[9] Journal of the American Chemical Society, 1974, vol. 96, p. 1565 - 1577
  • 2
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YieldReaction ConditionsOperation in experiment
89% With sulfuric acid; sodium hydrogencarbonate In methanol [Preparation of dimethyl 5-bromoisophthalate from 5-bromoisophthalic acid]
Into a 500 ml flask equipped with a stirrer and a Dimroth condenser, 110 g of 5-bromoisophthalic acid obtained above, 500 ml of methanol and 10 g of a concentrated sulfuric acid were placed and the resultant mixture was heated under the refluxing condition for 6 hours.
After the reaction mixture was cooled by being left standing, the cooled mixture was added dropwise to 1 liter of distilled water and the obtained mixture was neutralized with a 5percent by weight aqueous solution of sodium hydrogencarbonate.
The formed precipitates were separated by filtration and washed twice with 2 liters of distilled water.
The obtained white solid substance was dried at 50OEC under a reduced pressure for 2 days and 109 g (0.4 moles) of dimethyl 5-bromoisophthalate was obtained (the yield: 89percent).
Reference: [1] Patent: EP1346975, 2003, A1,
[2] Patent: WO2014/20350, 2014, A1,
[3] Patent: WO2014/20351, 2014, A1,
  • 3
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  • [ 51760-21-5 ]
YieldReaction ConditionsOperation in experiment
90%
Stage #1: With caesium carbonate In N,N-dimethyl-formamide at 20℃; for 0.5 h;
Stage #2: at 20℃;
5-bromobenzene-l, 3 -dicarboxylic acid (5 g, 20.4 mmol, 1.0 eq) was dissolved in DMF (150 mL). CS2CO3 (33.2 g, 102 mmol, 5.0 eq) was added and the reaction stirred for 30 min. Mel (7.2 g, 51 mmol, 2.5 eq) was added dropwise and the solution was stirred at room temperature overnight. Water was added and the aqueous layer was extracted with EtOAc. The combined organic extracts were dried (Na2S04), filtered and evaporated in vacuo to give the title compound as a colourless oil (5 g, 90 percent).LC-MS: m z 274.9 [M+H]
Reference: [1] Patent: WO2013/37705, 2013, A2, . Location in patent: Page/Page column 137
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  • [ 23351-91-9 ]
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YieldReaction ConditionsOperation in experiment
76.6% for 20 h; Reflux A solution of conc. sulphuric acid (8 ml) in methanol (30 ml) was added dropwise to a solution of B (13.2 g, 0.054 mol) in methanol (150 ml). The reaction mixture was refluxed for 20 h. Afier cooling to room temperature, the product was obtained as colourless crystals. After filtration, the product was washed with cold methanol to give C 11.3 g (Yield. 76.6percent). ‘H-NMR (CDC13): ö=3.96 (s, 6H), 8.35 (d, 2H), 8.6 (t, 1H).
76.6% for 20 h; Reflux A solution of conc. sulphuric acid (8 ml) in methanol (30 ml) was added dropwise to a solution of B (13.2 g,0.054 mol) in methanol (150 ml). The reaction mixture was refluxed for 20 h. After cooling to room temperature, the product was obtained as colourless crystals. After filtration, the product was washed with cold methanol to give C 11.3g (Yield. 76.6percent). 1H-NMR(CDCl3): δ = 3.96 (s, 6H), 8.35 (d, 2H), 8.6 (t, 1H).
Reference: [1] Inorganic Chemistry, 2016, vol. 55, # 16, p. 7928 - 7943
[2] Chemical Communications, 2015, vol. 51, # 40, p. 8508 - 8511
[3] Patent: US2015/152123, 2015, A1, . Location in patent: Paragraph 0156; 0159; 0160
[4] Patent: EP2876112, 2015, A1, . Location in patent: Paragraph 0163; 0165
[5] Journal of the American Chemical Society, 1974, vol. 96, p. 1565 - 1577
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  • [ 379711-34-9 ]
  • [ 244768-63-6 ]
  • [ 121-91-5 ]
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  • [ 23351-91-9 ]
YieldReaction ConditionsOperation in experiment
50.4% at 120℃; for 7 h; Into a 100 ml pressure and sealable glass tube, 9.70 g (50 mmol) of dimethyl isophthalate, 30.00 g of 10 wt percent fuming sulfuric acid and 10.40 g (100 mmol) of bromine were charged, and the content was stirred at 120° C. for 7 hours. After the conclusion of the reaction, the content was cooled to room temperature, and placed in a beaker containing ice water to give a solid. The resulting solid was filtered off, washed with cooling, and further dried under reduced pressure to give 11.95 g of a crude crystal of the aimed product (reaction yield: 50.4percent 5-bromoisophthalic acid, 19.6percent isophthalic acid, 4.9percent 2,5-dibromoisophthalic acid, 7.2percent 4,5-dibromoisophthalic acid, 7.0percent dimethyl 5-bromoisophthalate, 1.5percent dimethyl isophthalate, 0.9percent dimethyl 2,5-dibromoisophthalate and 0.2percent dimethyl 4,5-dibromoisophthalate). Then, dimethyl esters were derived from the crystal by heating and stirring it with 65.50 g (2.04 mol) of methanol and 1.75 g (30 mol percent) of sulfuric acid in an autoclave at 120° C. [0038] In succession, the esters were subjected to rectification to give 6.73 g (yield: 49.3percent, vacuum boiling point: 159° C./4.8mmHg) of aimed dimethyl 5-bromoisophthalate and 1.67 g (yield: 17.2percent, vacuum boiling point: 133° C./4.8mmHg) of dimethyl isophthalate corresponding to a raw material. The resulting crystals were identified as dimethyl 5-bromoisophthalate and 5-bromoisophthalic acid by MASS, 1H-NMR and melting point.
Reference: [1] Patent: US2004/15010, 2004, A1, . Location in patent: Page 4
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YieldReaction ConditionsOperation in experiment
86% at 55℃; for 25 h; 33.23 g (0.2 mol) of isophthalic acid and 37.42 g (0.12 mol) of silver sulphate are dissolved in 330 ml of sulphuric acid. 13.3 ml (0.26 mol) of bromine are then added over 1 h. The solution is heated at 55° C. for 24 h. The medium is then poured into ice, the insoluble material is filtered and taken up in ethyl acetate. The remaining solid is taken up in water and basified with a saturated aqueous sodium hydrogen carbonate solution. The insoluble material is filtered and the filtrate is acidified and then extracted with ethyl acetate. The organic phase is washed with water and then dried over magnesium sulphate and concentrated. [00640] White powder. m=42.1 g. Y=86percent. m.p.=285-7° C. 1H NMR (DMSO): 8.40 (2H, s), 8.57 (1H, t), 13.76 (2H, COOH, s).
86.7% at 60℃; for 32 h; A mixture ofA (12.2 g, 73.5 mmol), Ag2SO4 (13.3g, 43 mmol) and Br2 (5 ml, 97 mmol) in conc. sulphuric acid was stirred at 60° C. for 32 h. The excess of Br2 was removed by addition of saturated Na2S2O3 solution very slowly. The residue was poured into ice-watet The solids were isolated by filtration and given into a NaHCO3 solution. The AgBr was then removed by filtration. The solution was acidified with concentrated hydrochloric acid to give white precipitates. The solid was filtered and washed with water several times to give the product as white solid 20.5 g (Yield. 86.7percent). 1H-NMR (DMSO-d5): ö=8.23 (d, 2H), 8.40 (t, 1H).
86.7% With silver(II) sulfate; sulfuric acid; bromine In water at 60℃; for 32 h; A mixture of A (12.2 g, 73.5 mmol), Ag2SO4 (13.3 g, 43 mmol) and Br2 (5ml, 97 mmol) in conc. sulphuric acidwas stirred at 60°C for 32 h. The excess of Br2 was removed by addition of saturated Na2S2O3 solution very slowly. Theresidue was poured into ice-water. The solids were isolated by filtration and given into a NaHCO3 solution. The AgBrwas then removed by filtration. The solution was acidified with concentrated hydrochloric acid to give white precipitates.The solid was filtered and washed with water several times to give the product as white solid 20.5g (Yield. 86.7percent). 1HNMR(DMSO-d6): δ = 8.23 (d, 2H), 8.40 (t, 1H).
20% at 60℃; Into a 100-mL round-bottom flask, was placed a solution of isophthalic acid (10 g, 60 24 mmol, 1 00 equiv) in 980ZoH2SO4 (60 mL) This was followed by the addition of N-bromosuccimmide (12 80 g, 72 32 mmol, 1 20 equiv), in portions at 6O0C in 10 mm The resulting solution was stirred overnight at 6O0C in an oil bath The reaction was cooled to room temperature and then quenched by the addition of water/ice The solids were collected by filtration, and washed with 2x60 mL of hexane The solid was dried in an oven under reduced pressure The crude product was purified by re-crystallization from ethyl acetate to give 3 g (20percent) of 5-bromoisophthalic acid as a white solid.
13.2 g at 60℃; for 6 h; Isophthalic acid (II) (5 g, 60 mmol) was dissolved in concentrated sulfuric acid (30 mL) at room temperature and raised to 60 ° C. NBS (10.6 g, 60 mmol) was then added to the solution in three batches and 3 g was added every half hour. TLC followed the reaction. After the reaction was completed, the reaction solution was poured into ice (200 g) and precipitated as a white solid. Filtered, filtered with water (100 mL) and petroleum ether (50 mL). The solvent was evaporated to dryness using a rotary evaporator to give 13.2 g of 5-bromoisophthalic acid as a white solid in a yield of 90percent and used directly in the next step.

Reference: [1] Tetrahedron, 2001, vol. 57, # 24, p. 5027 - 5038
[2] Tetrahedron Letters, 2000, vol. 41, # 7, p. 1015 - 1018
[3] Journal of Organic Chemistry, 2007, vol. 72, # 15, p. 5867 - 5869
[4] Patent: US6689922, 2004, B1, . Location in patent: Page column 40-41
[5] Patent: US2015/152123, 2015, A1, . Location in patent: Paragraph 0156; 0157; 0158
[6] Patent: EP2876112, 2015, A1, . Location in patent: Paragraph 0163; 0164
[7] Chemical Communications, 2015, vol. 51, # 40, p. 8508 - 8511
[8] Patent: WO2010/78449, 2010, A2, . Location in patent: Page/Page column 310
[9] Asian Journal of Chemistry, 2015, vol. 27, # 8, p. 3127 - 3128
[10] Patent: CN106831397, 2017, A, . Location in patent: Paragraph 0006; 0010
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YieldReaction ConditionsOperation in experiment
34%
Stage #1: With potassium permanganate In water for 9 h; Heating / reflux
Stage #2: With hydrogenchloride In water at 20℃;
Placing Compound A in an amount of 25.2 g (136 mmol) and KMnO4 in an amount of 86.1 g (544 mmol) into a flask, and the resultant solution was reacted in water for 9 hours under refluxing. After the reaction terminated, a precipitate was filtered and the filtrate was processed with 6N hydrochloric acid at room temperature. A deposit was washed with the use of 0. 1N hydrochloric acid and dried, resultantly obtaining 11.4 g of Intermediate B (yield: 34 percent).
Reference: [1] Bioorganic and Medicinal Chemistry Letters, 1998, vol. 8, # 24, p. 3459 - 3464
[2] Patent: EP1640365, 2006, A1, . Location in patent: Page/Page column 65
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Reference: [1] Patent: US2003/229079, 2003, A1, . Location in patent: Page 32
[2] Patent: WO2006/55434, 2006, A2, . Location in patent: Page/Page column 67
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YieldReaction ConditionsOperation in experiment
50.4% With bromine In (2S)-N-methyl-1-phenylpropan-2-amine hydrate Example 18
Into a 100 ml pressure and sealable glass tube, 9.70 g (50 mmol) of dimethyl isophthalate, 30.00 g of 10 wtpercent fuming sulfuric acid and 10.40 g (100 mmol) of bromine were charged, and the content was stirred at 120°C for 7 hours.
After the conclusion of the reaction, the content was cooled to room temperature, and placed in a beaker containing ice water to give a solid.
The resulting solid was filtered off, washed with cooling, and further dried under reduced pressure to give 11.95 g of a crude crystal of the aimed product (reaction yield: 50.4percent 5-bromoisophthalic acid, 19.6percent isophthalic acid, 4.9percent 2,5-dibromoisophthalic acid, 7.2percent 4,5-dibromoisophthalic acid, 7.0percent dimethyl 5-bromoisophthalate, 1.5percent dimethyl isophthalate, 0.9percent dimethyl 2,5-dibromoisophthalate and 0.2percent dimethyl 4,5-dibromoisophthalate).
Reference: [1] Patent: EP1293495, 2003, A1,
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Reference: [1] Patent: EP1346975, 2003, A1,
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  • [ 23351-91-9 ]
YieldReaction ConditionsOperation in experiment
11.9% at 110 - 150℃; for 7 - 22 h; Into a 50 ml pressure and sealable glass tube, 1.66 g (10 mmol) of isophthalic acid, 6.00 g of 10 wt percent fuming sulfuric acid and 1.6 g (10 mmol) of bromine were charged, and the content was stirred at 130° C. for 22 hours. After the conclusion of the reaction, the content was cooled to room temperature, and placed in a beaker containing ice water to give a solid. The resulting solid was filtered off, washed with cooling, and further dried under reduced pressure to give 2.41 g (purity: 83.5percent) of a crude crystal of the aimed product (yield: 81.9percent). Then, the crystals were solved in 10 g of methanol at 60° C., cooled to room temperature, and thereafter filtered off to give 1.61 g (purity: 100percent) of a white crystal (yield of recrystallization: 80.1percent). This crystal was identified as 5-bromopisophthalic acid by MASS, 1H-NMR and melting point. EXAMPLES 2 TO 7 [0033] Procedures were carried out similarly to that of Example 1 except that the reaction temperature, the concentration of fuming sulfuric acid and the amount of bromine were changed. The results on the resulting monobromo products were shown in Table 1. [TABLE-US-00001] TABLE 1 Concentration of Fuming Quantitative Yield (percent) Ex. Sulfuric Acid Bromine Tempera- Time 4,5- 2,5- No. (wt percent)-(g) g(mmol) ture(° C.) (h.) 5BIP IP DBIP DBIP 2 10-6 1.6(10) 110 22 34.5 58.0 trace - 3 20-6 1.6(10) 110 22 48.6 43.2 trace - 4 30-6 1.6(10) 110 22 62.8 24.6 2.3 - 5 10-6 1.6(10) 150 22 77.0 4.1 8.0 - 6 20-6 1.6(10) 150 7 53.8 46.5 0.7 - 7 10-6 3.2(20) 150 7 79.1 6.4 5.8 trace IP: Isophthalic Acid, 5BIP:5-Bromoisophthalic Acid, 4,5-DBIP: 4,5-Dibromoisophthalic Acid 2,5-DBIP: 2,5-Dibromoisophthalic Acid EXAMPLE 8 [0034] Into a 50 ml pressure and sealable glass tube, 1.66 g (10 mmol) of isopthalic acid, 6.00 g of 30 wt percent fuming sulfuric acid and 1.6 g (10 mmol) of bromine were charged, and the content was stirred at 150° C. for 22 hours. After the conclusion of the reaction, the content was cooled to room temperature, and placed in a beaker containing ice water to give a solid. Then, the resulting solid was filtered off, washed with cooling, and further purified by column chromatography on silica gel (chloroform/methanol=6/1, v/v) to give 0.51 g (yield: 20.7percent) of 5-bromoisophthalic acid, 0.76 g (yield: 23.5percent) of 4,5-dibromoisophthalic acid and 0.07 g (yield: 2.1percent) of 2,5-dibromoisophthalic acid. These crystals were identified by MASS, 1H-NMR and melting point. EXAMPLES 9 TO 16 [0035] Procedures were carried out similarly to that of Example 8 except that the reaction temperature, the concentration of fuming sulfuric acid and the amount of bromine were changed. The results on the resulting monobromo and dibromo products were shown in Table 2. [TABLE-US-00002] TABLE 2 Concentration of Fuming Quantitative Yield (percent) Ex. Sulfuric Acid Bromine Tempera- Time 4,5- 2,5- No. (wt percent)-(g) g(mmol) ture(° C.) (h.) 5BIP IP DBIP DBIP 9 60-6 1.6(10) 110 22 45.0 1.4 18.7 1.0 10 20-6 1.6(10) 130 22 49.2 0.0 15.3 trace 11 30-6 1.6(10) 130 22 53.1 0.8 13.6 1.0 12 20-6 1.6(10) 150 22 43.1 0.0 20.0 0.8 13 20-6 3.2(20) 150 7 37.5 0.0 23.3 1.5 14 10-12 1.6(10) 150 7 47.0 0.6 18.1 1.2 15 20-12 1.6(10) 150 7 49.8 0.7 20.3 1.4 16 20-12 3.2(10) 150 7 11.9 0.0 26.2 4.9 IP: Isophthalic Acid, 5BIP:5-Bromoisophthalic Acid, 4,5-DBIP: 4,5-Dibromoisophthalic Acid 2,5-DBIP: 2,5-Dibromoisophthalic Acid
Reference: [1] Patent: US2004/15010, 2004, A1, . Location in patent: Page 3-4
[2] Organic Process Research and Development, 2002, vol. 6, # 5, p. 591 - 596
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  • [ 23351-91-9 ]
YieldReaction ConditionsOperation in experiment
50.4% at 120℃; for 7 h; Into a 100 ml pressure and sealable glass tube, 9.70 g (50 mmol) of dimethyl isophthalate, 30.00 g of 10 wt percent fuming sulfuric acid and 10.40 g (100 mmol) of bromine were charged, and the content was stirred at 120° C. for 7 hours. After the conclusion of the reaction, the content was cooled to room temperature, and placed in a beaker containing ice water to give a solid. The resulting solid was filtered off, washed with cooling, and further dried under reduced pressure to give 11.95 g of a crude crystal of the aimed product (reaction yield: 50.4percent 5-bromoisophthalic acid, 19.6percent isophthalic acid, 4.9percent 2,5-dibromoisophthalic acid, 7.2percent 4,5-dibromoisophthalic acid, 7.0percent dimethyl 5-bromoisophthalate, 1.5percent dimethyl isophthalate, 0.9percent dimethyl 2,5-dibromoisophthalate and 0.2percent dimethyl 4,5-dibromoisophthalate). Then, dimethyl esters were derived from the crystal by heating and stirring it with 65.50 g (2.04 mol) of methanol and 1.75 g (30 mol percent) of sulfuric acid in an autoclave at 120° C. [0038] In succession, the esters were subjected to rectification to give 6.73 g (yield: 49.3percent, vacuum boiling point: 159° C./4.8mmHg) of aimed dimethyl 5-bromoisophthalate and 1.67 g (yield: 17.2percent, vacuum boiling point: 133° C./4.8mmHg) of dimethyl isophthalate corresponding to a raw material. The resulting crystals were identified as dimethyl 5-bromoisophthalate and 5-bromoisophthalic acid by MASS, 1H-NMR and melting point.
Reference: [1] Patent: US2004/15010, 2004, A1, . Location in patent: Page 4
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Reference: [1] Journal of the Chemical Society, Perkin Transactions 2: Physical Organic Chemistry (1972-1999), 1984, # 3, p. 529 - 532
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YieldReaction ConditionsOperation in experiment
12.8 g With copper(I) oxide; sodium hydroxide In water at 130℃; for 20 h; Arranged with the magnetic to the 250 ml round-bottom flask, add 5 - between bromine benzene phthalic acid (20 g, 80 mmol), water (64 ml) and sodium hydroxide (16 g, 400 mmol). Further to this mixed solution of a catalytic amount of cuprous oxide (0.5 g). Then raising the temperature to 130 °C, reflux about 20 h. TLC tracking reaction, after the reaction is complete. The reaction solution was transferred to a dropping funnel, slowly drop added to the citrate 15percent HCl (82 ml) of 250 ml round bottom flask, adding while stirring, white solid precipitated. Mixed solution to rise to 60 - 70 °C, stirring 1 h. Cooling to room temperature, filtered, the filter cake is water (200 ml) washing 3 times. After drying, to obtain white solid 12.8 g, yield 86percent. The product can be directly used for the next step reaction.
Reference: [1] Patent: CN106831397, 2017, A, . Location in patent: Paragraph 0006; 0010
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Reference: [1] Bioorganic and Medicinal Chemistry Letters, 1998, vol. 8, # 24, p. 3459 - 3464
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  • [ 120173-41-3 ]
Reference: [1] Tetrahedron Letters, 2000, vol. 41, # 7, p. 1015 - 1018
[2] Patent: JP2015/224231, 2015, A,
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  • [ 160892-07-9 ]
Reference: [1] Journal of Heterocyclic Chemistry, 1994, vol. 31, # 6, p. 1417 - 1420
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  • [ 161796-10-7 ]
Reference: [1] Patent: WO2013/37705, 2013, A2,
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  • [ 944392-68-1 ]
Reference: [1] Chemical Communications, 2015, vol. 51, # 40, p. 8508 - 8511
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  • [ 453566-14-8 ]
Reference: [1] Patent: WO2013/37705, 2013, A2,
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  • [ 23351-91-9 ]
  • [ 453566-15-9 ]
Reference: [1] Patent: WO2013/37705, 2013, A2,
  • 22
  • [ 23351-91-9 ]
  • [ 677010-20-7 ]
Reference: [1] Patent: US2015/152123, 2015, A1,
[2] Patent: EP2876112, 2015, A1,
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