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[ CAS No. 120077-67-0 ] {[proInfo.proName]}

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Chemical Structure| 120077-67-0
Chemical Structure| 120077-67-0
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CAS No. :120077-67-0 MDL No. :MFCD17779947
Formula : C9H8BrClO2 Boiling Point : -
Linear Structure Formula :- InChI Key :-
M.W : 263.52 Pubchem ID :-
Synonyms :

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Application In Synthesis of [ 120077-67-0 ]

* 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 [ 120077-67-0 ]

[ 120077-67-0 ] Synthesis Path-Downstream   1~5

  • 1
  • [ 64-17-5 ]
  • [ 25118-59-6 ]
  • [ 120077-67-0 ]
YieldReaction ConditionsOperation in experiment
97% With sulfuric acid;Reflux; A solution of <strong>[25118-59-6]4-bromo-3-chlorobenzoic acid</strong> (24.5 g, 104.05 mmol) and concentrated sulfuric acid (11.09 mL, 208.10 mmol) in EtOH (245 mL) was heated under reflux overnight. The reaction mixture was cooled, and concentrated under reduced pressure. To the residue was added ethyl acetate, and the organic layer was washed with water, aqueous sodium hydrogen carbonate solution and brine. Then, the organic layer was dried over sodium sulfate, and the solvent was evaporated under reduced pressure to give ethyl 4-bromo-3-chlorobenzoate (26.6 g, 101 mmol, 97%) as a pale orange solid. 1H NMR (300 MHz, CDCl3):delta 1.40(3H,t,J=7.0 Hz), 4.38(2H,q,J=7.2 Hz), 7.59-7.73(1H,m), 7.74-7.87(1H,m), 8.11(1H,d,J=1.5 Hz).
96% With sulfuric acid; for 4h;Inert atmosphere; Reflux; Step 1: ethyl 4-bromo-3-chlorobenzoateA solution of <strong>[25118-59-6]4-bromo-3-chlorobenzoic acid</strong> (5 g, 21 .23 mmol) and H2S04 (5 mL) in EtOH (50 mL) was heated under reflux for 4 hr under nitrogen atmosphere. The mixture was cooled down to rt and quenched with water (100 mL). The solution was extracted with EA (150 mL x 3), washed with saturated NaHC03 (500 mL x 3), dried over anhydrous Na2S04 and concentrated in vacuo to afford ethyl 4-bromo-3-chlorobenzoate (5.39 g, 96%) as a colorless oil.
88% With sulfuric acid; at 0 - 85℃; Example 5; l-(4-(5-(8-Bromo-6-(trifluoromethyl)imidazo[l,2-fl]pyridin-2-yl)-l,2,4-oxadiazol-3-yl)-3- chlorobenzyl)azetidine-3-carboxylic acid; Ethyl 3-chloro-4-bromo benzoate (34). To a stirred solution of intermediate 33 (10 g, 43 mmol) in EtOH (50 rnL) was added concentrated H2SO4 (20 mL) at 0 0C. After the addition was complete, the reaction was stirred at 85 0C for 4 h. After completion, the reaction mixture was concentrated in vacuo and the residue was dissolved in DCM. The organic layer was washed with water, aqueous sodium bicarbonate solution, and saturated NaCl. The organic layers were combined, dried over Na2SO4, and concentrated in vacuo to afford the title intermediate 34 as an off-white solid (10 g, yield 88%).
With sulfuric acid; In water; for 60h;Heating / reflux; Description for D22Ethyl 4-bromo-3-chlorobenzoate (D22) <n="47"/>To a suspension of <strong>[25118-59-6]4-bromo-3-chlorobenzoic acid</strong> (5.00 g, 21.2 mmol) in ethanol (50 ml.) was added sulphuric acid (5 mL) and the resultant mixture heated to reflux for 60 h. The reaction was partitioned between ethyl acetate (50 mL) and water (50 mL). The aqueous layer was extracted with further ethyl acetate and the combined organic fractions dried (phase separator) and concentrated in vacuo to give the title compound as a brown oil/solid (5.09 g, 19.3 mmol). deltaH (d6-DMSO, 400 MHz): 8.06 (1 H, d), 7.96 (1 H, d), 7.80 (1 H, dd), 4.33 (2H, q), 1.33 (3H, t). MS (ES): no mass ion observed.
With sulfuric acid; for 60h;Heating / reflux; To a suspension of <strong>[25118-59-6]4-bromo-3-chlorobenzoic acid</strong> (5.00 g, 21.2 mmol) in ethanol (50 ml.) was added sulphuric acid (5 mL) and the resultant mixture heated to reflux for 60 h. The reaction was partitioned between ethyl acetate (50 mL) and water (50 mL). The aqueous layer was extracted with further ethyl acetate and the combined organic fractions dried (phase separator) and concentrated in vacuo to give the title compound as a brown oil/solid (5.09 g, 19.3 mmol). deltaH (d6-DMSO, 400 MHz): 8.06 (1 H, d), 7.96 (1 H, d), 7.80 (1 H, dd), 4.33 (2H, q), 1.33 (3H, t).
With thionyl chloride; at 0 - 60℃; for 16h; To a solution of <strong>[25118-59-6]4-bromo-3-chlorobenzoic acid</strong> (21 .23 mmol, 5 g) in dry ethanol (30 ml_) at 05C, thionyl chloride (1 .8 eq. 38.2 mmol. 2.79 ml) was added dropwise. The mixture was stirred at 605C for 16h. Solvent was evaporated and the crude product was dissolved with EtAcO. The solution was washed with saturated NaHC03 aqueous solution, brine, dried over anhydrous MgS04, filtered and concentrated to dryness to afford the title compound which was used in the next step without further purification (5.60 g., Yield: 100%). LC-MS: tR = 2.79 [M+H] + = not ion (method 6)

  • 2
  • [ CAS Unavailable ]
  • [ 120077-67-0 ]
  • [ 120077-68-1 ]
YieldReaction ConditionsOperation in experiment
With ammonium chloride In dichloromethane; toluene iii (iii) (iii) 4-Bromo-3-chlorobenzyl alcohol To a solution of ethyl 4-bromo-3-chlorobenzoate (1.0 g.), in dry dichloromethane at 0° was added diisobutyl aluminium hydride (7.8 g. IM solution in toluene) over 20 minutes. The mixture was stirred at 20° overnight. Saturated ammonium chloride was added until solid formed.
  • 3
  • [ 82765-44-4 ]
  • [ 120077-67-0 ]
YieldReaction ConditionsOperation in experiment
With copper(I) bromide; sodium nitrite; In water; hydrogen bromide; (ii) Ethyl 4-bromo-3-chlorobenzoate To a suspension of <strong>[82765-44-4]ethyl 3-chloro-4-aminobenzoate</strong> (9.9 g.) in hydrobromic acid (48%, 30 ml.) at 0 was added a freshly prepared solution of sodium nitrite (4.6 g.) in water (12 ml.) over 20 minutes (keeping the temperature at 0) to form a diazonium salt. A solution of cuprous bromide (14 g.) in hydrobromic acid (48%, 40 ml.) was heated to 50 and the diazonium salt was added as a slurry and the resulting mixture refluxed for 30 minutes. After cooling the mixture was poured onto ice/water (300 ml.) and the product extracted into ethyl acetate. The organic layer was dried over anhydrous magnesium sulphate and evaporated to give a solid.
  • 4
  • [ 120077-67-0 ]
  • [ 120077-68-1 ]
YieldReaction ConditionsOperation in experiment
72% Stage #1: 4-bromo-3-chlorobenzoic acid ethyl ester With lithium aluminium tetrahydride In tetrahydrofuran at -15 - 0℃; for 2h; Inert atmosphere; Stage #2: With water; ammonium chloride In tetrahydrofuran 9.2 Step 2: (4-bromo-3-chlorophenyl)methanolTo a solution of LAH (0.672 g, 17.6 mmol) in dry THF (80 mL) was added ethyl 4- bromo-3-chlorobenzoate (4.2 g, 16 mmol) in THF (20 mL) at -15°C under nitrogenatmosphere and the mixture was stirred at 0°C for 2 hr. The reaction was quenched with sat. NH4CI (50 mL), extracted with EA (100 mL x 3), dried over anhydours Na2S04. After the removal of solvent, the crude residue was purified by column chromatography to afford (4- bromo-3-chlorophenyl)methanol (2.57 g, 72%) as a colorless oil.
  • 5
  • [ 120077-67-0 ]
  • [ 1261685-26-0 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: N,N-dimethyl-formamide / 140 °C 2: sodium hydroxide; water / methanol; tetrahydrofuran / 10 - 35 °C
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