ChemicalBook CAS DataBase List 2-BROMO-5-METHOXYBENZOIC ACID

2-BROMO-5-METHOXYBENZOIC ACID synthesis

11synthesis methods

Product Name:2-BROMO-5-METHOXYBENZOIC ACID
CAS Number:22921-68-2
Molecular formula:C8H7BrO3
Molecular Weight:231.04

7507-86-0 Synthesis

7507-86-0
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$7.00/1g

22921-68-2
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$6.00/5g

Yield:22921-68-2 100%

Reaction Conditions:

with sodium chlorite;sodium dihydrogenphosphate;2-methyl-but-2-ene in tetrahydrofuran;water;tert-butyl alcohol at 20; for 1.16667 h;

Steps:

2-Bromo-5-methoxybenzoic acid (4a).

). 2-Bromo-5-methoxybenzaldehyde (548 mg, 2.5 mmol), tert-butyl alcohol (30 mL), 2-methyl-2-butene (6 mL), and THF (30 mL) were addedto a round-bottom flask. NaClO₂ (811 mg, 7.1 mmol) and NaH₂PO₄(2.14 g, 14 mmol) dissolved in water were gradually added over a period of 10min and the resulting mixture was stirred for 1.0 hr at room temperature. Afterthe removal of tert-butyl alcohol, 2-methyl-2-butene, and THF under reduced pressure, 2M HCl was added to the reaction mixture to acidify it (pH 2). The solution was thenextracted with ethyl acetate. The organic phase was washed with brine and driedover anhydrous Na₂SO₄. The solvent was removed underreduced pressure. The white solid (616 mg, quantitative yield) was identifiedas 2-bromo-5-methoxybenzoic acid (4a) on the basis of ¹H-NMRand mass spectra. ¹H-NMR (400 MHz, CDCl₃): d 3.84 (s, -OCH₃, 3H), 6.95 (dd, J=8.8 Hz, 3.0 Hz, 1H), 7.50 (d, J=3.0 Hz, 1H), 7.58 (d, J=8.8 Hz, 1H); MS (ESI): m/z[M-H+2]^- 231, [M-H]^- 229.

References:

Ohe, Tomoyuki;Umezawa, Ryutaro;Kitagawara, Yumina;Yasuda, Daisuke;Takahashi, Kyoko;Nakamura, Shigeo;Abe, Akiko;Sekine, Shuichi;Ito, Kousei;Okunushi, Kentaro;Morio, Hanae;Furihata, Tomomi;Anzai, Naohiko;Mashino, Tadahiko [Bioorganic and Medicinal Chemistry Letters,2018,vol. 28,# 23-24,p. 3708 - 3711] Location in patent:supporting information

586-38-9 Synthesis