ChemicalBook CAS DataBase List 4-DIFLUOROMETHOXY-3-METHOXY-BENZALDEHYDE

4-DIFLUOROMETHOXY-3-METHOXY-BENZALDEHYDE synthesis

5synthesis methods

Product Name:4-DIFLUOROMETHOXY-3-METHOXY-BENZALDEHYDE
CAS Number:162401-70-9
Molecular formula:C9H8F2O3
Molecular Weight:202.15

1895-39-2
284 suppliers
$6.00/5g

121-33-5 Synthesis

121-33-5
1089 suppliers
$9.00/1g

4-DIFLUOROMETHOXY-3-METHOXY-BENZALDEHYDE

162401-70-9
129 suppliers
$15.00/1g

Yield: 91%

Reaction Conditions:

with caesium carbonate in DMF (N,N-dimethyl-formamide);water at 100; for 3.5 h;

Steps:

A solution of 4-hydroxy-3-methoxybenzaldehyde (2.0 g, 0.013 mol), sodium 2-chloro- 2, 2-difluoroacetate (4.8 g, 0.031 mol) and cesium carbonate (72 mg, 0.018 mol) in DMF (14 mL) and water (14 mL) was heated at 100°C for 3.5 hours. The mixture was acidified with concentrated hydrochloric acid and extracted with ethyl acetate (2x 25 mL). The organic layer was washed with water (2x25 mL), dried (MgSO4) and the solvent removed under reduced pressure. Purification by column chromatography with silica gel and ethyl acetate/n-hexane (1: 4) as eluent gave 4-(difluoromethoxy)-3-methoxybenzaldehyde (2.41 g, 91%) as an oil. 8 (250 MHz, CDCI3) : 3.76 (s, 3H); 6.49 (t, JF-H=74. 0 Hz, 1H) ; 7.11 (d, J=8.0 Hz, 1H) ; 7.27 (dd, Je=1. 7 Hz, J2=8.0 Hz, 1 H) ; 7.31 (d, J=1.7 Hz, 1 H) ; 9.74 (s, 1 H).

References:

ALMIRALL PRODESFARMA SA WO2005/58883, 2005, A1 Location in patent:Page/Page column 131