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Chemical Structure| 264272-63-1 Chemical Structure| 264272-63-1

Structure of 264272-63-1

Chemical Structure| 264272-63-1

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Product Details of [ 264272-63-1 ]

CAS No. :264272-63-1
Formula : C9H7BrO4
M.W : 259.05
SMILES Code : COC(=O)C1=C(Br)C=C(C=C1)C(O)=O
MDL No. :MFCD00100645

Safety of [ 264272-63-1 ]

GHS Pictogram:
Signal Word:Warning
Hazard Statements:H315-H319-H335
Precautionary Statements:P261-P264-P271-P280-P302+P352-P304+P340-P305+P351+P338-P312-P362-P403+P233-P501

Application In Synthesis of [ 264272-63-1 ]

* 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 [ 264272-63-1 ]

[ 264272-63-1 ] Synthesis Path-Downstream   1~3

  • 1
  • [ 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).
  • 2
  • [ 91760-66-6 ]
  • [ 264272-63-1 ]
  • 3
  • [ 264272-63-1 ]
  • [ 18643-86-2 ]
YieldReaction ConditionsOperation in experiment
98% With thionyl chloride; In methanol; for 5h;Reflux; Step 2: Preparation of dimethyl 2-bromoterephthalate To a solution of 3-bromo-4-(methoxycarbonyl)benzoic acid (3.0 g, 11.6 mmol) in MeOH (50 mL) was slowly added SOCl2 (2.76 g, 23.2 mmol) dropwise. After the addition completion, the reaction mixture was refluxed for 5 h. Then MeOH was removed and water was added. It was extracted with EA and the organic layer was washed with aqueous sodium bicarbonate solution, brine, dried over Na2SO4, filtered and concentrated under reduced pressure to give dimethyl 2-bromoterephthalate (3.1 g, yield 98%) as a white solid. It was used without further purification in the next step.
 

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