4-Chloro-2-methoxybenzaldehyde → 1-(4-Chloro-2-methoxyphenyl)propan-1-one

4-Chloro-2-methoxy-benzaldehyde (0.54 g, 3.2 mmol) in 10 mL of THF was treated with 3.0 M EtMgBr (2 mL, 6.0 mmol) at room temperature. The solution was stirred for 1 hour and quenched with MeOH. The solution was poured into water, treated 10 mL of 10% HCl, extracted with EtOAc several times. The combined organic layers were washed brine, dried (MgSO4), filtered, and concentrated. The residue was diluted with CH2Cl2, treated with PCC (1.33 g, 6.4 mmol) for 2 hours. The reaction mixture was filtered through a pack of silica gel to give 0.42 g of the title compound. MS (DCI) m/e 199 (M+H)+.

1. customquenched with MeOH
2. additionThe solution was poured into water
3. additiontreated 10 mL of 10% HCl
4. extractionextracted with EtOAc several times
5. washThe combined organic layers were washed brine
6. dry with materialdried (MgSO4)
7. filtrationfiltered
8. concentrationconcentrated
9. additionThe residue was diluted with CH2Cl2
10. filtrationThe reaction mixture was filtered through a pack of silica gel

ORD-Eintrag

ord-255ec494d5f245e1888e65ce9141fd9c

Quelldatensatz

uspto-grants-2008_11

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US07456169B2