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[ CAS No. 249647-24-3 ]

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Chemical Structure| 249647-24-3
Chemical Structure| 249647-24-3
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CAS No. :249647-24-3 MDL No. :MFCD07778512
Formula : C8H6BrIO2 Boiling Point : 328.1°C at 760 mmHg
Linear Structure Formula :- InChI Key :-
M.W :340.94 g/mol Pubchem ID :17750019
Synonyms :

Safety of [ 249647-24-3 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P280-P305+P351+P338 UN#:N/A
Hazard Statements:H302 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 249647-24-3 ]

  • Upstream synthesis route of [ 249647-24-3 ]
  • Downstream synthetic route of [ 249647-24-3 ]

[ 249647-24-3 ] Synthesis Path-Upstream   1~4

  • 1
  • [ 249647-24-3 ]
  • [ 249647-25-4 ]
Reference: [1] Journal of Medicinal Chemistry, 1999, vol. 42, # 20, p. 4088 - 4098
  • 2
  • [ 106896-49-5 ]
  • [ 249647-24-3 ]
YieldReaction ConditionsOperation in experiment
55%
Stage #1: With hydrogenchloride; sodium nitrite In water; acetone at 0℃; for 2 h;
Stage #2: With potassium iodide In water; acetone at 0 - 20℃; for 1 h;
A solution of 4-amino-3-bromo-benzoic acid methyl ester (5.0 g, 22.0 mmol from Aldrich) in acetone (35 mL) was treated with 6M HCl (35 mL). The solution was cooled to 0° C. and treated dropwise with NaNO2 (1.84 g, 26.1 mmol) dissolved in 10 mL water. After stirring for 2 hours at 0° C., the reaction was slowly treated with potassium iodide (5.47 g, 32.6 mmol) dissolved in 20 mL water. The reaction mixture was allowed to warm to room temperature and stir for 1 hour. Reaction mixture was diluted with water and extracted with EtOAc (2×150 mL). The combined organic phase was dried (Na2SO4) and concentrated under vacuum. The residue was chromatographed (80 g Redi-Sep column) eluting from 100percent heptane to 20:80 EtOAc:heptane to afford the intermediate (4.1 g, 55percent) as a solid. 1HNMR (CDCl3) δ ppm: 8.27 (1H), 7.98 (1H), 7.64 (1H), 3.94 (3H).
55%
Stage #1: With hydrogenchloride; sodium nitrite In water; acetone at 0℃; for 2 h;
Stage #2: With potassium iodide In water; acetone at 0 - 20℃; for 1 h;
A solution of 4-amino-3-bromo-benzoic acid methyl ester (5.0 g, 22.0 mmol from Aldrich) in acetone (35 mL) was treated with 6M HCl (35 mL).
The solution was cooled to 0° C. and treated dropwise with NaNO2 (1.84 g, 26.1 mmol) dissolved in 10 mL water.
After stirring for 2 hours at 0° C., the reaction was slowly treated with potassium iodide (5.47 g, 32.6 mmol) dissolved in 20 mL water.
The reaction mixture was allowed to warm to room temperature and stir for 1 hour.
Reaction mixture was diluted with water and extracted with EtOAc (2*150 mL).
The combined organic phase was dried (Na2SO4) and concentrated under vacuum The residue was chromatographed (80 g Redi-Sep column) eluting from 100percent heptane to 20:80 EtOAc:heptane to afford the intermediate (4.1 g, 55percent) as a solid. 1HNMR (CDCl3): 8.27 (1H), 7.98 (1H), 7.64 (1H), 3.94 (3H).
Reference: [1] Angewandte Chemie - International Edition, 2008, vol. 47, # 42, p. 8108 - 8111
[2] Patent: US2012/232026, 2012, A1, . Location in patent: Paragraph 0440; 0441
[3] Patent: US2012/35122, 2012, A1, . Location in patent: Paragraph 0760; 0761
[4] Organic and Biomolecular Chemistry, 2012, vol. 10, # 25, p. 4907 - 4915
  • 3
  • [ 619-44-3 ]
  • [ 249647-24-3 ]
Reference: [1] Journal of Medicinal Chemistry, 1999, vol. 42, # 20, p. 4088 - 4098
  • 4
  • [ 6311-37-1 ]
  • [ 249647-24-3 ]
Reference: [1] Organic and Biomolecular Chemistry, 2012, vol. 10, # 25, p. 4907 - 4915
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