ChemicalBook CAS DataBase List METHYL 4-BROMO-2-HYDROXYBENZOATE

METHYL 4-BROMO-2-HYDROXYBENZOATE synthesis

5synthesis methods

Product Name:METHYL 4-BROMO-2-HYDROXYBENZOATE
CAS Number:22717-56-2
Molecular formula:C8H7BrO3
Molecular Weight:231.04

1666-28-0 Synthesis

1666-28-0
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$9.00/1g

22717-56-2
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$6.00/250mg

Yield: 93%

Reaction Conditions:

with sulfuric acid in methanol for 19 h;Reflux;

Steps:

2 Methyl 4-bromo-2-hydroxybenzoate (INT1)
A solution of 2-hydroxy-4-bromobenzoic acid (4.57 g, 1.0 equiv., 20.0 mmol) in anhydrous MeOH (60 ml_) was transferred to a flame-dried one-necked flask (100 ml_) equipped with a stirrer bar. Subsequently, addition of concentrated sulfuric acid (98.5%, 2.2 ml_) was performed. The mixture was stirred at reflux for 19 hours before being concentrated. After evaporation of the solvent, addition of EtOAc (60 ml_) and careful addition of saturated aqueous NaHCC (80 ml_) was made, and the phases were separated. The aqueous phase was extracted with EtOAc (3x50 ml_) and the organic phase was washed with brine (100 ml_), before being dried over sodium sulphate, filtered and concentrated to yield a dark brown crude isolate. The crude material was purified by flash column chromatography on silica gel using an eluent system of Heptane/EtOAc 90: 10 to afford the desired product as colorless needles (4.31g, 18.7 mmol, 93%). TLC (Heptane: EtOAc, 90: 10 v/v, UV, KMn0₄): Rf= 0.38; ^.H NMR (400 MHz, CDCb): d 10.83 (s, 1H), 7.68 (d, J = 8.5 Hz, 1H), 7.18 (d, J = 1.9 Hz, 1H), 7.02 (dd, J = 5.5 Hz, 1.9 Hz, 1H), 3.95 (s, 3H);¹³C NMR (101 MHz, CDCb): d 170.3, 162.1, 131.0, 130.1, 122.9, 121.0, 111.5, 52.7; IR (ATR, CH2CI2): 3155, 2954, 1677, 1606, 1570, 1480, 1439, 1330, 1282, 1204,1095, 885, 772, 1765 cm ¹; HRMS (m/z): [M] calcd. for CsHeBrC, 228.9506; found, 228.9516.

References:

AARHUS UNIVERSITET WO2021/110968, 2021, A1 Location in patent:Page/Page column 39; 40

67-56-1 Synthesis