ChemicalBook CAS DataBase List 4-FLUORO-3-METHOXYBENZOIC ACID

4-FLUORO-3-METHOXYBENZOIC ACID synthesis

5synthesis methods

Product Name:4-FLUORO-3-METHOXYBENZOIC ACID
CAS Number:82846-18-2
Molecular formula:C8H7FO3
Molecular Weight:170.14

74385-37-8

82846-18-2

The general procedure for the synthesis of 3-methoxy-4-fluorobenzoic acid from methyl 4-fluoro-3-methoxybenzoate was as follows: methyl 4-fluoro-3-methoxybenzoate (11 g, 59.8 mmol) was dissolved in methanol (100 mL), and a solution of sodium hydroxide (9.5 g, 240 mmol) in water (20 mL) was added, and the reaction was stirred for 4 h at room temperature. Upon completion of the reaction, the solvent was removed by distillation under reduced pressure to give a residue. The residue was dissolved in water (100 mL) and the pH was adjusted with 1N HCl solution to 4. Subsequently, the precipitated solid was collected by filtration, washed with water (3 x 50 mL), and dried to give 3-methoxy-4-fluorobenzoic acid as a white solid (9 g, 97% yield). The product was characterized by 1H-NMR (300 MHz, DMSO-d6): δ 7.66-7.55 (m, 2H), 7.37-7.30 (m, 1H), 3.91 (s, 3H).

74385-37-8
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$20.00/250mg

82846-18-2
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$6.00/250mg

Yield: 97%

Reaction Conditions:

with water;sodium hydroxide in methanol at 20; for 4 h;

Steps:

79.2 Step 2: 4-fluoro-3-methoxybenzoic acid
A solution of methyl 4-fluoro-3-methoxybenzoate (11 g, 59.8 mmol) in methanol (100 mL) was treated with sodium hydroxide (9.5 g, 240 mmol) in water (20 mL) for 4h at room temperature. The solvent was removed in vacuo to afford a residue, which was dissolved in water (100 mL) and the pH value was adjusted to 4 with HC1 (IN). The solids were collected by filtration, washed with water (3 x 50 mL) and dried to afford 4-fluoro-3-methoxybenzoic acid as a white solid (9 g, 97 %). *H-NMR (300 MHz, DMSO) δ 7.66-7.55(m, 2H), 7.37-7.30(m, 1H), 3.91(s, 3H)

References:

BIOENERGENIX;MCCALL, John;KELLY, Robert, C.;ROMERO, Donna, L. WO2014/66795, 2014, A1 Location in patent:Paragraph 0175