Alternatived Products of [ 842136-27-0 ]
Product Details of [ 842136-27-0 ]
CAS No. : | 842136-27-0 |
MDL No. : | MFCD24107212 |
Formula : |
C9H9BrO2
|
Boiling Point : |
- |
Linear Structure Formula : | - |
InChI Key : | - |
M.W : |
229.07
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Pubchem ID : | - |
Synonyms : |
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Safety of [ 842136-27-0 ]
Application In Synthesis of [ 842136-27-0 ]
* 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.
- Upstream synthesis route of [ 842136-27-0 ]
- Downstream synthetic route of [ 842136-27-0 ]
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[ 5469-19-2 ]
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[ 842136-27-0 ]
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[ 5469-19-2 ]
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[ 842136-27-0 ]
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[ 276677-03-3 ]
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[ 615-87-2 ]
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[ 152849-72-4 ]
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[ 611-01-8 ]
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[ 842136-27-0 ]
Yield | Reaction Conditions | Operation in experiment |
78% |
With N-Bromosuccinimide; trifluoroacetic acid; at 50℃; for 16h; |
A mixture of 2,4-dimethylbenzoic acid (4.5 g, 30 mmol) and NBS (5.34 g, 30 mmol) in TFA (100 mL) was stirred at 50 C for 16 h. The solvent was removed in vacuo and the resulting residue was purified by recrystallization using EtOAc twice to afford 5-bromo-2,4- dimethylbenzoic acid (5.36 g, 23.4 mmol, 78%) as a white solid. ESI-MS (EI, m/z): 229 [M+H]t ?HNIVIR (500 IVIHz, CDC13): 8.23 (s, 1H), 7.15 (s, 1H), 2.57 (s, 3H), 2.42 (s, 3H). |
65% |
With bromine; sodium hydroxide; In water; at 20℃; for 3h; |
[01254] Step l : 5-bromo-2,4-dimethylbenzoic acid[01255] To the stirred solution of NaOH (60 g) in water (1 152 ml) was added bromine (36 ml) dropwise at 0 C and stirred the reaction mixture for 45 min. at same temperature. 2,4- dimethylbenzoic acid ( 12 g, 79.9 mmol) was added in above reaction mixture at 0 C portion wise and stirred the reaction at room temperature for 3h. After completion of reaction of reaction (TLC) reaction mixture was acidified using cone. HC1, solid was filtered through Buchner funnel and wash with water and dried to afford the desired compound (12 g, 65 %) which was used without further purification. |
Reference:
[1]Patent: WO2018/89433,2018,A1 .Location in patent: Paragraph 00364; 00490; 00497; 00521; 00551
[2]Patent: WO2012/142513,2012,A1 .Location in patent: Page/Page column 318
[3]Journal of the American Chemical Society,1935,vol. 57,p. 718
[4]Journal of the American Chemical Society,1935,vol. 57,p. 718
[5]Chemische Berichte,1884,vol. 17,p. 1608
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[ 124-38-9 ]
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[ 5469-19-2 ]
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[ 7697-37-2 ]
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[ 276677-03-3 ]
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[ 611-01-8 ]
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[ 1255206-85-9 ]
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[ 842136-27-0 ]
Yield | Reaction Conditions | Operation in experiment |
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With N-Bromosuccinimide In trifluoroacetic acid at 50℃; |
A
2,4-Dimethylbenzoic acid (7.00 g, 46.6 mmol) and NBS (12.4 g, 69.9 mmol) were dissolved in TFA (150 mL). The mixture was then heated at 500C for overnight. Analysis by LC as well as TLC (hexanes/EtOAc - 1/1) indicated that reaction had gone to completion. The solvent was removed in vacuo and the resulting residue was dissolved in DCM, absorbed onto silica gel, and loaded onto a silica MPLC column for separation. The desired product was separated using the solvent system of hexanes/EtOAc (1/1) to yield 3-bromo-2,4-dimethylbenzoic acid. The undesired isomeric 5-bromo-2,4-dimethylbenzoic acid was also isolated. 1H-NMR (CDCI3, 500 MHz)9 δ 7.868 (d, J = 7.5 Hz, IH), 7.2 (d, J = 7.5 Hz, IH), 2.793 (s, 3H), 2.526 (s, 3H) |
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[ 152849-72-4 ]
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[ 842136-27-0 ]
Yield | Reaction Conditions | Operation in experiment |
92.9% |
With water; lithium hydroxide; In tetrahydrofuran; at 70.0℃; for 3.0h;Inert atmosphere; |
A mixture of methyl 5-bromo-2,4-dimethyl-benzoate (400 mg, 1.65 mmol), LiOH (197 mg, 8.21 mmol) in tetrahydrofuran (3 mL) and water (3 mL) was stirred under N2 at 70 C. for 3 h. The reaction was then diluted with 30 mL of water and 20 mL of EtOAc. The mixture was then adjusted pH to 4-5 with 1N HCl. The organic layer was concentrated to dryness to give the title compound as a white solid (350 mg, 92.9% yield). LCMS (ESI) [M+H]+=230.9. |