ChemicalBook CAS DataBase List Methyl 7-bromo-3-hydroxy-2-naphthoate

Methyl 7-bromo-3-hydroxy-2-naphthoate synthesis

6synthesis methods

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

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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]

67-56-1 Synthesis