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[ CAS No. 18643-86-2 ]

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Chemical Structure| 18643-86-2
Chemical Structure| 18643-86-2
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Product Details of [ 18643-86-2 ]

CAS No. :18643-86-2 MDL No. :MFCD00060638
Formula : C10H9BrO4 Boiling Point : 252.8°C at 760 mmHg
Linear Structure Formula :- InChI Key :N/A
M.W :273.08 g/mol Pubchem ID :-
Synonyms :

Safety of [ 18643-86-2 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P261-P305+P351+P338 UN#:N/A
Hazard Statements:H302-H315-H317-H319-H335 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 18643-86-2 ]

  • Downstream synthetic route of [ 18643-86-2 ]

[ 18643-86-2 ] Synthesis Path-Downstream   1~15

  • 1
  • [ 67-56-1 ]
  • [ 586-35-6 ]
  • [ 18643-86-2 ]
YieldReaction ConditionsOperation in experiment
98% With sulfuric acid; for 5h;Reflux; 2-Bromo terephthalic acid (204 mmol,Methanol (MeOH) 0.4M and20 mmol of sulfuric acid (H2SO4) was added to a round flask, and the mixture was refluxed for 5 hours. Next, the reaction solution was filtered and washed to obtain a reaction product in a yield of 98%
93% With thionyl chloride; at 0 - 20℃; Example 13Dimethyl 2-bromoterephthalate; Intermediate-4 To a round bottom flask was added <strong>[586-35-6]2-bromoterephthalic acid</strong> (10.0 g, 40.8 mmol) in methanol (120 mL). The suspension was cooled to 0 C. and thionyl chloride (11.9 mL, 163 mmol) was added dropwise. The reaction mixture was allowed to warm to rt and was stirred overnight. The mixture was concentrated, sat. NaHCO3 was added and extracted with DCM (3×). The combined organic phases were then washed with water, and brine, dried over anhydrous Na2SO4, filtered and concentrated to afford dimethyl 2-bromoterephthalate (10.4 g, 93%). LC-MS: (FA) ES+274; 1H NMR (400 MHz, CDCl3) delta 8.31 (d, J=1.6 Hz, 1H), 8.00 (dd, J=8.1, 1.6 Hz, 1H), 7.81 (d, J=8.1 Hz, 1H), 3.96 (s, 3H), 3.95 (s, 3H).
92% With sulfuric acid; at 60℃; for 6h;Inert atmosphere; Large scale; In nitrogen atmosphere, <strong>[586-35-6]2-bromoterephthalic acid</strong> (30.0 kg, 122.4mol) was suspened in methanol (95 kg), cooled to about 5 C, and 98 weight % sulfuric acid (33.0 kg) was added and the mixture was stirred at 60 C for 6 hours. TLC is confirmed for the end of reaction, the reaction mixture is then cooled to the room temperature, methyl tert-butyl ether (220.0 kg) was added and the organic layer was washed with water (180.0 kg), and NaHCO3 aqueous solution (8 weight %, 180.0 kg) and salt water (24 weight %, 180.0 kg) , dried using anhydrous magnesium sulfate (6.0 kg) , concentrated under reduced pressure to obtain the title compound as pale yellow crystals (30.40 kg, yield 92.0%).
83% With thionyl chloride; at 0 - 20℃;Inert atmosphere; To a solution of <strong>[586-35-6]2-bromoterephthalic acid</strong> (2.0 g, 8.2 mmol) in MeOH (20 mL) at 0 00 underN2was added thionyl chloride (5.8 g, 49 mmol) dropwise. The resulting mixture was stirred atroom temperature overnight. The mixture was concentrated and the residue partitioned between DCM (20 mL) and saturated aqueous NaHCO3 (15 mL). The aqueous phase was extracted with DCM (3 x 10 mL). The combined organic fractions were washed with saturated aqueous NaHCO3 (3 x 10 mL), brine (3 x 10 mL), dried (Na2SO4), filtered and concentrated to give the title compound (1.85 g, 83%) as a white solid. 1H NMR (400 MHz,ODd3) 6 8.30 (d, J = 1.6 Hz, 1 H), 7.99 (dd, J = 8.0, 1.2 Hz, 1 H), 7.80 (d, J = 8.0 Hz, 1 H),3.95 (s, 3H), 3.94 (s, 3H); LCMS RT 2.63 mm; m/z 273,275 [M+H]+
To a mixture of <strong>[586-35-6]2-bromoterephthalic acid</strong> (2.0 g, 8.2 mmol) and DMF (0.3 mL) in DCM (20 mL) was added oxalyl chloride (15.6 g, 123 mmol) and the mixture stirred at room (0570) temperature overnight. The reaction was then concentrated and the residue diluted with MeOH (50 mL) at 0 C and stirred for 10 min. The solvent was removed under reduced pressure to give the title product as a yellow oil that was used for the next step directly. LCMS: RT 2.61 min; m/z 273.0, 275.0 [M+H] +.

  • 2
  • [ 67-56-1 ]
  • [ 13815-89-9 ]
  • [ 18643-86-2 ]
YieldReaction ConditionsOperation in experiment
5.5 g With triethylamine; at 0 - 20℃; for 2h;Inert atmosphere; A solution of 2-bromoterephthalic acid (5.000 g, 20.41 mmol) in thionyl chloride (20.00 mL, 273 mmol) was heated at 100C for 5 h. The dark colored reaction mass was cooled to room temperature and solvent was evaporated off under reduced pressure. The residual mass was cooled to OoC and methanol (20 ml) and triethylamine (5 ml, 35.5 mmol) were added slowly under nitrogen. The reaction mixture was then stirred for 2 h at ambient temperature. The solution was evaporated to dryness under reduced pressure. The residual mass was dissolved in ethylacetate (100 ml) and washed with water (2X 25ml), followed by 2N HCI (2X 25 ml) and finally with saturated sodium bicarbonate solution. Combined organic layers were dried over sodium sulfate and evaporated under reduced pressure to obtain dimethyl 2-bromobenzene-1 ,4-dicarboxylate (5.5 g, 99% of theoretical yield) as a white solid. H NMR (400 MHz, CHLOROFORM-c/) δ ppm 3.95 (d, J=1 .25 Hz, 3 H) 3.96 (d, J=1 .25 Hz, 3 H) 7.81 (dd, J=8.03, 1.25 Hz, 1 H) 8.00 (d, J=8.03 Hz, 1 H) 8.31 (s, 1 H) MS [M-H] " : 272.9/ 273.9 (rt 1.90-1.97 min)
  • 3
  • [ 18643-86-2 ]
  • [ 264272-63-1 ]
YieldReaction ConditionsOperation in experiment
24% With potassium hydroxide; acetic acid; In methanol; ethyl acetate; toluene; Petroleum ether; Example 76 Preparation of 3-bromo-4-(methoxycarbonyl)benzoic Acid Potassium hydroxide (2.87 g, 51 mmol) was added to a solution of 2-bromo-1,4-benzenedicarboxylic acid, dimethyl ester (14 g, 51 mmol) in methanol (50 mL) at 25 C. The reaction mixture was stirred at 25 C. for 24 h and then at 50 C. for 3 h. The solvent was concentrated under reduced pressure and the residue was diluted with water (100 mL) and extracted with ethyl acetate (2*200 mL). The water layer was acidified to pH 2 with 2N hydrochloric acid solution and extracted with ethyl acetate (2*200 mL). The combined organic layers were washed with brine (100 mL), dried (MgSO4), filtered and concentrated in vacuo. The resulting solid was boiled in toluene (100 mL) and the insolubles were removed by filtration. The filtrate was concentrated to dryness under reduced pressure and the resulting solid was flash chromatographed (silica gel, 50% ethyl acetate in petroleum ether with 1% acetic acid) to give 3-bromo-4-(methoxycarbonyl)benzoic acid (3.28 g, 24% yield) as a colorless solid.
24% With potassium hydroxide; acetic acid; In methanol; ethyl acetate; toluene; Petroleum ether; Example 2 Preparation of 2-bromo-1,4-benzenedicarboxylic acid, 1-methyl ester Potassium hydroxide (2.87 g, 51 mmol) was added to a solution of 2-bromo-1,4-benzenedicarboxylic acid, dimethyl ester (14 g, 51 mmol) in methanol (50 mL) at 25 C. The reaction mixture was stirred at 25 C. for 24 h, and then at 50 C. for 3 h. The solvent was concentrated under reduced pressure and the residue was diluted with water (100 mL) and extracted with ethyl acetate (2*200 mL). The water layer was acidified to pH 2 with 2 M HCl and extracted with ethyl acetate (2*200 mL). The combined organic layers were washed with brine (100 mL), dried (MgSO4), filtered, and concentrated. The resulting solid was boiled in toluene (100 mL) and the insolubles were filtered. The filtrate was concentrated and the resulting solid was flash chromatographed (silica, 50% ethyl acetate in petroleum ether with 1% acetic acid) to give 2-bromo-1,4-benzenedicarboxylic acid, 1-methyl ester (3.28 g, 24%) as a white solid.
With sodium hydroxide; water; In methanol; at 20℃; for 1.5h; To a solution of <strong>[18643-86-2]dimethyl 2-bromoterephthalate</strong> (1.04 g) in methanol (10 mL) was added 1 N sodium hydroxide (5.71 mL) at room temperature. After stirring for 1.5 hour, the reaction was quenched by adding 1 N hydrochloric acid (7 mL). White crystals were formed. Water (10 mL) was added to aid crystalyzation. The crystals were collected by filtration, washed with water, and dried in the air.3-Bromo-4- (methoxycarbonyl) benzoic acid was obtained as white crystals (532 mg). 3-bromo-4- (methoxycarbonyl) benzoic acid 'H-NMR (DMSO-d6) δ 3.89 (3H, s), 7.87 (1H, d, J = 8 Hz), 8.01 (1H, d, J = 8 Hz), 8.17 (1H, s).
  • 4
  • [ 18643-86-2 ]
  • [ 30240-01-8 ]
  • 5
  • [ 120-61-6 ]
  • [ 18643-86-2 ]
  • 6
  • [ 18643-86-2 ]
  • [ 13052-77-2 ]
  • [ 893415-43-5 ]
  • 7
  • [ 577-19-5 ]
  • [ 18643-86-2 ]
  • 2'-nitro-biphenyl-2,5-dicarboxylic acid dimethyl ester [ No CAS ]
  • 8
  • [ 592-31-4 ]
  • [ 18643-86-2 ]
  • methyl 3-butyl-2,4-dioxo-1,2,3,4-tetrahydroquinazoline-7-carboxylate [ No CAS ]
  • 9
  • [ 110-85-0 ]
  • [ 18643-86-2 ]
  • [ 898547-76-7 ]
YieldReaction ConditionsOperation in experiment
With caesium carbonate;palladium diacetate; 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene; In 1,4-dioxane; at 100℃; for 24h; 1.80 g of piperazine, 1.0 g of <strong>[18643-86-2]dimethyl 2-bromoterephthalate</strong>, 720 mg of 9,9-diemthyl-4,5-bis(diphenylphosphino)xanthene, 280 mg of palladium(II) acetate and 2.20 g of cesium carbonate are dissolved in 40 ml of 1,4-dioxane and stirred at 100 C. under an argon atmosphere for 24 hours. The reaction mixture is diluted with 100 ml of dichloromethane and extracted with 50 ml of saturated sodium bicarbonate solution and 50 ml of saturated sodium chloride solution. The organic phases is dried over MgSO4 and then the solvent is removed in vacuo. 330 mg of dimethyl 2-piperazin-1-yl terephthalate are obtained as an oil. C14H18N204 (278.31), LCMS (ESI): 279.3 (M+H+).
  • 10
  • [ 18643-86-2 ]
  • [ 62-53-3 ]
  • [ 566155-74-6 ]
  • 11
  • [ 18643-86-2 ]
  • C23H20N2O2 [ No CAS ]
  • 12
  • [ 18643-86-2 ]
  • C18H18N2O2 [ No CAS ]
  • 13
  • [ 18643-86-2 ]
  • C21H16N2O2 [ No CAS ]
  • 14
  • [ 18643-86-2 ]
  • C22H18N2O2 [ No CAS ]
  • 15
  • [ 18643-86-2 ]
  • C22H18N2O2 [ No CAS ]
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