ChemicalBook CAS DataBase List 2,4-Difluoro-6-methoxybenzaldehyde

2,4-Difluoro-6-methoxybenzaldehyde synthesis

6synthesis methods

Product Name:2,4-Difluoro-6-methoxybenzaldehyde
CAS Number:608515-57-7
Molecular formula:C8H6F2O2
Molecular Weight:172.13

4885-02-3 Synthesis

4885-02-3
182 suppliers
$10.00/1g

93343-10-3
240 suppliers
$15.00/5G

608515-57-7
19 suppliers
$90.00/50mg

256417-10-4 Synthesis

256417-10-4
146 suppliers
$11.00/1g

Yield:256417-10-4 19% ，608515-57-7 62%

Reaction Conditions:

titanium tetrachloride in dichloromethane at 0; for 1 h;

Steps:

(Intermediates 26A and 26B were prepared in a similar manner to the preparation described in WO 2004046133). To a stirred solution of 3,5- difluoroanisole (l.Og, 7.0 mmol) in dichloromethane (6 mL) at 0 0C was added dropwise titanium tetrachloride (1.23 mL, 11.2 mmol) and dichloromethyl methyl ether (0.63 mL, 7.0 mmol). Upon completion of addition, the reaction mixture was stirred for Ih and then poured into ice-water (50 mL). The resulting mixture was extracted with dichloromethane (3x 50 mL). The combined organics were washed with H2O (50 mL), brine (50 mL), dried over Na2SO4 and filtered. The volatiles were removed under reduced pressure to provide a residue. The residue was subjected to chromatography on silica gel eluting with 0 to 20% EtOAc/hexanes to give 2,6- difluoro-4-methoxybenzaldehyde, Intermediate 26 A [less polar material, 230 mg, 19%, 1H NMR (400 MHz, CDCl3) ? ppm 3.85 (s, 3 H), 6.47 (d, J=10.55 Hz, 2 H), 10.17 (s, 1 H)] and 2,4-difluoro-6-methoxybenzaldehyde, Intermediate 26B [more polar material, 740 mg, 62%, 1H NMR (400 MHz, CDCl3) ? ppm 3.91 (s, 3 H) 6.43 - 6.51 (m, 2 H) 10.30 (s, 1 H)], both as white solids.

References:

WO2007/30582,2007,A2 Location in patent:Page/Page column 90

4885-02-3 Synthesis

4885-02-3
182 suppliers
$10.00/1g

93343-10-3
240 suppliers
$15.00/5G

608515-57-7
19 suppliers
$90.00/50mg

References