5-fluoro-2-hydroxy-4-methoxybenzaldehyde synthesis

4synthesis methods

Product Name:5-fluoro-2-hydroxy-4-methoxybenzaldehyde
CAS Number:1311271-24-5
Molecular formula:C8H7FO3
Molecular Weight:170.14

155831-46-2
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5-fluoro-2-hydroxy-4-methoxybenzaldehyde

1311271-24-5
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Yield:1311271-24-5 71%

Reaction Conditions:

Stage #1: 2,4-dimethoxy-5-fluorobenzaldehydewith boron trichloride in dichloromethane at 0 - 20; for 24 h;Inert atmosphere;
Stage #2: with water in dichloromethane at 0;Inert atmosphere;

Steps:

5-Fluoro-4-methoxy-2-(methoxymethoxy)benzyl acetate (8).

To a stirring suspension of 5-fluoro-2,4-dimethoxybenzaldehyde (0.20 g, 1.09 mmol) in CH2Cl2 (3 mL) at 0 °C under Ar atmosphere was added BCl3 (1.0 M, 1.80 mL, 1.80 mmol) quickly, and the reaction mixture was allowed to attain room temperature slowly. After stirring for 24 h at room temperature, the reaction mixture was cooled to 0 °C and very slowly quenched with water (10 mL) and diluted with CH2Cl2 (10 mL). The organic layer was washed with water, brine, dried over Na2SO4 and then concentrated in vacuo to give a white solid which was further purified by column chromatography on silica (20% EtOAc/hexanes) to furnish 5-fluoro-2-hydroxy-4-methoxybenzaldehyde (0.13 g, 0.76 mmol, 71 %).

References:

Radomkit, Suttipol;Sarnpitak, Pakornwit;Tummatorn, Jumreang;Batsomboon, Paratchata;Ruchirawat, Somsak;Ploypradith, Poonsakdi [Tetrahedron,2011,vol. 67,# 21,p. 3904 - 3914] Location in patent:supporting information; experimental part

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17715-70-7
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