methyl 6-fluoro-3,4-dihydro-2H-chromene-2-carboxylate Chemical Properties

Melting point:

48 °C

Boiling point:

286.8±40.0 °C(Predicted)

Density 

1.242±0.06 g/cm3(Predicted)

storage temp. 

Sealed in dry,Room Temperature

solubility 

Dichloromethane, Methanol

form 

powder to crystal

color 

White to Light yellow

InChI

InChI=1S/C11H11FO3/c1-14-11(13)10-4-2-7-6-8(12)3-5-9(7)15-10/h3,5-6,10H,2,4H2,1H3

InChIKey

QAYAXMIKHJVIJM-UHFFFAOYSA-N

SMILES

C1(C(OC)=O)OC2=CC=C(F)C=C2CC1

CAS DataBase Reference

874649-82-8

Safety Information

HS Code 

2932.99.9090

methyl 6-fluoro-3,4-dihydro-2H-chromene-2-carboxylate Usage And Synthesis

Uses

Intermediate in the preparation of hydroxylated Nebivolol metabolites.

Synthesis

Example 2 Synthesis of methyl 6-fluoro-1-benzopyran-2-carboxylate: 20 g of 6-fluoro-4-oxo-4H-1-benzopyran-2-carboxylic acid (96 mmol) was mixed with 2 g of methanesulfonic acid (20 mmol) and 2 g of 5% Pd/C catalyst (Escat 112 type, Engelhard) in THF at 45-55°C under 4 bar of hydrogen pressure The hydrogenation reaction was carried out until the consumption of hydrogen stopped. The reaction progress was monitored by TLC. Upon completion of the reaction, the catalyst was removed by filtration and the reaction mixture was concentrated under reduced pressure to 40 ml. Subsequently, 100 ml of methanol was added and the mixture was stirred at 20-25 °C until the TLC assay showed less than 1% of 6-fluoro-3,4-dihydro-2H-chromene-2-carboxylic acid. Next, the solution was concentrated under reduced pressure, the residue was dissolved in 60 ml of THF and concentrated again under reduced pressure and the water was removed by azeotropic distillation. Finally 20 g of methyl 6-fluorochroman-2-carboxylate was obtained (yield: 100%). δH (400 MHz; CDCl3) 6.89-6.79 (2H, m, Ar), 6.77-6.76-6.72 (1H, m, Ar), 4.73-4.69 (1H, m), 3.79 (3H, s), 2.87-2.69 (2H, m) , 2.31-2.12 (2H, m).

References

[1] Patent: US2011/237808, 2011, A1. Location in patent: Page/Page column 5

methyl 6-fluoro-3,4-dihydro-2H-chromene-2-carboxylate(874649-82-8)Related Product Information

• Potassium hydrogen fluoride
• 6-Fluoro-3,4-dihydro-2H-1-benzopyran-2-carboxylic acid
• 4-Fluorophenoxyacetic acid
• methyl 6-fluoro-3,4-dihydro-2H-chromene-2-carboxylate