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Methyl 7-bromo-3-hydroxy-2-naphthoate synthesis
- Product Name:Methyl 7-bromo-3-hydroxy-2-naphthoate
- CAS Number:10155-36-9
- Molecular formula:C12H9BrO3
- Molecular Weight:281.1
![7-BROMO-3-HYDROXY-NAPHTHALENE-2-CARBOXYLIC ACID](/CAS/GIF/1779-11-9.gif)
1779-11-9
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![Iodomethane](/CAS/GIF/74-88-4.gif)
74-88-4
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![Methyl 7-bromo-3-hydroxy-2-naphthoate](/CAS/20210111/GIF/10155-36-9.gif)
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Yield: 99%
Reaction Conditions:
Stage #1:7-bromo-3-hydroxy-2-naphthoic acid with potassium carbonate in N,N-dimethyl-formamide at 20; for 1 h;
Stage #2:methyl iodide in N,N-dimethyl-formamide at 20; for 12 h;
Steps:
Methyl 7-bromo-3-hydroxy-2-naphthoate (62).
61 (500mg, 1.87mmol) was added to a suspension of K2CO3 (129mg, 0.94mmol) in anhydrous DMF (18mL). The reaction was stirred for 1h, and then methyl iodide (174μL, 2.81mmol) was added. The reaction was stirred for 12hat room temperature, and then concentrated under reduced pressure. The solid was taken up in a 1:1 mixture of ethyl acetate and water (50ml each). The aqueous layer was removed and the organic layer was washed with water (2×10mL) and then brine (10mL). After drying over MgSO4, the solvent was removed under reduced pressure, and the product obtained by flash chromatography (0→25% EtOAc in hexane) to give 62 as white crystals (525mg, 99%); mp: 153-155°C; 1H NMR (500MHz, CDCl3) δ 10.46 (s, 1H, -OH), 8.39 (d, J=0.7Hz, 1H, ArH), 7.95 (dd, J=1.4 & 0.7Hz, 1H, ArH), 7.57-7.54 (m, 2H, ArH), 7.29 (s, 1H, ArH), 4.03 (s, 3H, -CO2CH3); 13C (125MHz, CDCl3) δ 170.0, 156.7, 136.2, 132.3, 131.3, 130.9, 128.0, 127.9, 117.4, 115.0, 111.9, 52.7; HRMS-CI calcd for C12H10O3Br [M+ H]+ 279.9727; found 279.9735.
References:
Irvine, Mark W.;Fang, Guangyu;Sapkota, Kiran;Burnell, Erica S.;Volianskis, Arturas;Costa, Blaise M.;Culley, Georgia;Collingridge, Graham L.;Monaghan, Daniel T.;Jane, David E. [European Journal of Medicinal Chemistry,2019,vol. 164,p. 471 - 498]
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![7-BROMO-3-HYDROXY-NAPHTHALENE-2-CARBOXYLIC ACID](/CAS/GIF/1779-11-9.gif)
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![Methyl 7-bromo-3-hydroxy-2-naphthoate](/CAS/20210111/GIF/10155-36-9.gif)
10155-36-9
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762-72-1
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109-97-7
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![Methyl 4,7-dibromo-3-hydroxy-naphthalene-2-carboxylate](/CAS/20210305/GIF/1160295-91-9.gif)
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![Ethanamine, N-[(3,5-dichlorophenyl)methylene]-2,2-diethoxy-](/CAS/20210305/GIF/1000210-73-0.gif)
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![Methyl 7-bromo-3-hydroxy-2-naphthoate](/CAS/20210111/GIF/10155-36-9.gif)
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![7-BROMO-3-HYDROXY-NAPHTHALENE-2-CARBOXYLIC ACID](/CAS/GIF/1779-11-9.gif)
1779-11-9
123 suppliers
$6.00/250mg
![Methyl 7-bromo-3-hydroxy-2-naphthoate](/CAS/20210111/GIF/10155-36-9.gif)
10155-36-9
23 suppliers
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