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[ CAS No. 137242-41-2 ] {[proInfo.proName]}

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Chemical Structure| 137242-41-2
Chemical Structure| 137242-41-2
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Product Details of [ 137242-41-2 ]

CAS No. :137242-41-2 MDL No. :MFCD09952364
Formula : C11H9BrO3 Boiling Point : -
Linear Structure Formula :- InChI Key :-
M.W : 269.09 Pubchem ID :-
Synonyms :

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Application In Synthesis of [ 137242-41-2 ]

* 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 [ 137242-41-2 ]

[ 137242-41-2 ] Synthesis Path-Downstream   1~2

  • 1
  • [ 623-73-4 ]
  • [ 1761-61-1 ]
  • [ 137242-41-2 ]
YieldReaction ConditionsOperation in experiment
75% Stage #1: diazoacetic acid ethyl ester; 5-bromosalicyclaldehyde With tetrafluoroboric acid diethyl ether In dichloromethane at 38℃; Stage #2: With sulfuric acid In dichloromethane for 0.333333h; Synthesisof Compound 14 HBF4·Et2O(16.2 g, 99.5 mmol) was added to a solution of compound 13 in CH2Cl2 (500 mL), and then a solution ofethyldiazoacetate (180 g, 1.42 mol) in CH2Cl2 (500mL) was introduced as evolution of N2 gas while the reaction was notallowed over 38 oC. Once gas evolution ceased, the reaction mixturewas concentrated by rotary evaporator and conc. H2SO4(129 g, 1.29 mol, 98%) was added to the mixture while stirring. After 20minutes, the acidic mixture was neutralized with Na2CO3 (aq.).After the mixture was stored and crystallized overnight, compound 14 (100 g, yield: 75%) was obtained byfiltration. 1H-NMR (CDCl3, 400 MHz) d 8.25 (s,1H), 8.15~8.21 (m, 1H), 7.44~7.50 (m, 1H), 7.37~7.42 (m, 1H), 4.41 (q, J = 7.2 Hz, 2H), 1.43 (t, J = 7.2 Hz, 3H).
75% With tetrafluoroboric acid diethyl ether complex In dichloromethane at 38℃; 1.1 Stev 1 - Synthesis of ethyl 5-bromobenzofuran-3-carboxylate Stev 1 - Synthesis of ethyl 5-bromobenzofuran-3-carboxylate HBF4Et2O (16.2 g, 99.5 mmol) was added to a solution of 5-bromo-2- hydroxybenzaldehyde (200 g, 995 mmol) in CH2C12 (500 mL), and then a solution of ethyldiazoacetate (180 g, 1.42 mol) in CH2C12 (500 mL) was introduced as evolution of N2 gas while the reaction was not allowed over 38 °C. Once gas evolution ceased, the reaction mixture was concentrated by rotary evaporator and conc. H2S04 (129 g, 1.29 mol, 98%) was added to the mixture while stirring. After 20 minutes, the acidic mixture was neutralized with Na2CO3 (a.q.). After the mixture was stored and crystallized overnight, ethyl 5-bromobenzofuran-3-carboxylate(100 g, yield: 75%) was obtained by filtration. ‘H-NMR (CDC13, 400 MHz) 8.25 (s, 1H),8.15-8.21 (m, 1H), 7.44-7.50 (m, 1H), 7.37-7.42 (m, 1H), 4.41 (q, J= 7.2 Hz, 2H), 1.43 (t, J=7.2 Hz, 3H). MS (M+H7: 269 / 271.
75% With C4H10O*BF4*H(1+) In dichloromethane at 38℃; Inert atmosphere; 1.1 Step 1 - Synthesis of ethyl 5-bromobenzofuran-3-carboxylate 0HBF4Et2O (16.2 g, 99.5 mmol) was added to a solution of 5-bromo-2- hydroxybenzaldehyde (200 g, 995 mmol) in CH2C12 (500 mL), and then a solution of ethyl diazoacetate (180 g, 1.42 mol) in CH2C12 (500 mL) was introduced as evolution of N2 gas whilethe reaction was not allowed over 38 °C. Once gas evolution ceased, the reaction mixture was concentrated by rotary evaporator and conc. H2S04 (129 g, 1.29 mol, 98%) was added to the mixture while stirring. After 20 minutes, the acidic mixture was neutralized with Na2CO3 (a.q). After the mixture was stored and crystallized overnight, ethyl 5-bromobenzofuran-3-carboxylate (100 g, yield: 75%) was obtained by filtration. ‘H-NMR (CDC13, 400 MHz) 8.25 (s, 1H),8.15-8.21 (m, 1H), 7.44-7.50 (m, 1H), 7.37-7.42 (m, 1H), 4.41 (q, J= 7.2 Hz, 2H), 1.43 (t, J=7.2 Hz, 3H). MS (M+H): 269 / 271.
75% With tetrafluoroboric acid diethyl ether In dichloromethane at 38℃; 1.1 Synthesis of eth l 5-bromobenzofuran-S-carboxylate HBF4-Et20 (16.2 g, 99.5 mmol) was added to a solution of 5-bromo-2- hydroxybenzaldehyde (200 g, 995 mmol) in CH2C12 (500 mL), and then a solution of ethyl diazoacetate (180 g, 1.42 mol) in CH2C12 (500 mL) was introduced as evolution of N2 gas while the reaction was not allowed over 38 °C. Once gas evolution ceased, the reaction mixture was concentrated by rotary evaporator and cone. H2S04 (129 g, 1.29 mol, 98%) was added to the mixture while stirring. After 20 minutes, the acidic mixture was neutralized with Na2C03 (a.q.). After the mixture was stored and crystallized overnight, ethyl 5-bromobenzofuran-3-carboxylate (100 g, yield: 75%) was obtained by filtration. 1H- MR (400 MHz, CDC13) δ 8.25 (s, 1H),8.15-8.21 (m, 1H), 7.44-7.50 (m, 1H), 7.37-7.42 (m, 1H), 4.41 (q, J= 7.2 Hz, 2H), 1.43 (t, J = 7.2 Hz, 3H).
75% With tetrafluoroboric acid diethyl ether In dichloromethane at 38℃; 1.1 Step 1 - Synthesis of ethyl 5-bromobenzofuran-3-carboxylate HBF -Et20 (16.2 g, 99.5 mmol) was added to a solution of 5-bromo-2- hydroxybenzaldehyde (200 g, 995 mmol) in CH2C12 (500 mL), and then a solution of ethyl diazoacetate (180 g, 1.42 mol) in CH2C12 (500 mL) was introduced as evolution of N2 gas while the reaction was not allowed over 38 °C. Once gas evolution ceased, the reaction mixture was concentrated by rotary evaporator and cone. H2S04 (129 g, 1.29 mol, 98%) was added to the mixture while stirring. After 20 minutes, the acidic mixture was neutralized with Na2C03 (a.q.). After the mixture was stored and crystallized overnight, ethyl 5-bromobenzofuran-3-carboxylate (100 g, yield: 75%) was obtained by filtration. 1H- MR (CDC13; 400 MHz) δ 8.25 (s, 1H), 8.15-8.21 (m, 1H), 7.44-7.50 (m, 1H), 7.37-7.42 (m, 1H), 4.41 (q, J= 7.2 Hz, 2H), 1.43 (t, J = 7.2 Hz, 3H). MS (M+H)+: 269 / 271.
75% Stage #1: diazoacetic acid ethyl ester; 5-bromosalicyclaldehyde With tetrafluoroboric acid diethyl ether In dichloromethane at 38℃; Inert atmosphere; Stage #2: With sulfuric acid In dichloromethane for 0.333333h; 1.1 Step I- Svnthesis o(ethvl 5-bromobenzo(uran-3-carboxvlate HBF4·Et20 (16.2 g, 99.5 mmol) was added to a solution of5-bromo-2-hydroxybenzaldehyde (200 g, 995 mmol) in CH2Cb (500 mL), and then a solution of ethyldiazoacetate (180 g, 1.42 mol) in CH2Cb (500 mL) was introduced as evolution ofN2 gas while5 the reaction was not allowed over 38 °C. Once gas evolution ceased, the reaction mixture wasconcentrated by rotary evaporator and cone. H2S04 (129 g, 1.29 mol, 98%) was added to themixture while stirring. After 20 minutes, the acidic mixture was neutralized with Na2C03 (a.q).After the mixture was stored and crystallized overnight, ethyl 5-bromobenzofuran-3-carboxylate(100 g, yield: 75%) was obtained by filtration. 1H-NMR (CDCh, 400 MHz) 8 8.25 (s, 1H),10 8.15~8.21 (m, 1H), 7.44~7.50 (m, 1H), 7.37~7.42 (m, 1H), 4.41 (q, J = 7.2 Hz, 2H), 1.43 (t, J =7.2 Hz, 3H). MS (M+Ht: 269 I 271.
With tetrafluoroboric acid diethyl ether In dichloromethane at 0 - 20℃; for 1h; 11 Scheme 10.1 Ethyl diazoacetate (1.38 g, 12.09 mmol) dropwise was added to a mixture of 5-bromo-2-hydroxybenzaldehyde (1.21 g, 6.05 mmol) and 50% w/w HBF4 * Et20 (0.20 g, 0.60 mmol) in DCM (30 mmol) at 0°C to form a reaction mixture. After addition, the reaction mixture was slowly warmed to room temperature and stirred for 1 hour. After the hemiacetal intermediate was formed, concentrated H2S04 (3 mL) was added into the reaction mixture and stirred for further 1 hour. After the reaction was completed, the solvent in the reaction mixture was removed under reduced pressure. The residual was neutralized with saturated Nal ICO3 and extracted with EtOAc; and the resulting organic layers were combined. The combined organic layers were dried over MgS04 and concentrated in vacuo to obtain a crude product. The crude product was used as Compound 75, ethyl 5-bromobenzofuran-3-carboxylate, in the next step without further purification.

  • 2
  • [ 137242-41-2 ]
  • [ 1595284-72-2 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: nitric acid / chloroform / 2.5 h / -20 - 0 °C 2: iron; ammonium chloride / tetrahydrofuran; methanol; water / 3 h / Reflux 3: lithium hydroxide monohydrate / water; 1,4-dioxane / 2 h / Reflux
Multi-step reaction with 3 steps 1: nitric acid / chloroform / 2.5 h / -20 - 0 °C 2: ammonium chloride; iron / methanol; water; tetrahydrofuran / 3 h / Reflux 3: lithium hydroxide monohydrate; water / 1,4-dioxane / 2 h / Reflux
Multi-step reaction with 3 steps 1: nitric acid / chloroform / 2.5 h / -20 - 0 °C 2: iron; ammonium chloride / methanol; tetrahydrofuran; water / 3 h / Reflux 3: lithium hydroxide monohydrate; water / 1,4-dioxane / 2 h / Reflux
Multi-step reaction with 3 steps 1: nitric acid / chloroform / 2.5 h / -20 - 0 °C 2: iron; ammonium chloride / methanol; tetrahydrofuran; water / 3 h / Reflux 3: lithium hydroxide monohydrate; water / 1,4-dioxane / 2 h / Reflux
Multi-step reaction with 3 steps 1: nitric acid / chloroform / 2.5 h / -20 - 0 °C 2: ammonium chloride; iron / methanol; tetrahydrofuran; water / 3 h / Reflux 3: lithium hydroxide; water / 1,4-dioxane / 2 h / Reflux
Multi-step reaction with 3 steps 1: nitric acid / chloroform / 2.5 h / -20 - 0 °C 2: methanol; iron; ammonium chloride / tetrahydrofuran; water / 3 h / Reflux 3: lithium hydroxide monohydrate / 1,4-dioxane / 2 h / Reflux

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