Benzaldehyde, 3-(1,1,2,2-tetrafluoroethoxy)- → HCID 59379235, compound

Temperature

-78 °C

To a solution of dichlorophenylmethyl sulfoxide (5.94 g, 28.4 mmol; K. C. Tin & T. Dust, Tetra. Lett. 1970, 4643) in THF (100 mL) at −78° C. was added LDA (1.8 M in THF, 20.5 mL, 36.9 mmol). The reaction mixture was stirred at −78° C. for 15 min and then was added 3-(1,1,2,2-tetrafluoro-ethoxy)-benzaldehyde (6.94 g, 31.3 mmol). After stirring at −78° C. for 45 min, EtMgBr (1.0 M solution in t-BuOMe, 60 mL, 60 mmol) was added. The reaction mixture was stirred at −78° C. for another 40 min, quenched with NH4Cl aqueous solution and acidified with 1 N HCl. The organic layer was separated and the aqueous layer was extracted with CH2Cl2. The combined organic phases were dried (Na2SO4), concentrated and purified by column chromatography to give 4.13 g (49%) of A2a as a yellow oil: 1H NMR (300 MHz, CDCl3) δ 7.89 (dd, J=7.6, 2.6 Hz, 1H), 7.81 (s, 1H), 7.58-7.46 (m, 2H), 5.95 (tt, J=53.0, 2.7 Hz, 1H), 4.68 (s, 2H); MS (ES) m/z: 293 (M+Na+).

1. stirringAfter stirring at −78° C. for 45 min
2. stirringThe reaction mixture was stirred at −78° C. for another 40 min
3. customquenched with NH4Cl aqueous solution
4. customThe organic layer was separated
5. extractionthe aqueous layer was extracted with CH2Cl2
6. dry with materialThe combined organic phases were dried (Na2SO4)
7. concentrationconcentrated
8. custompurified by column chromatography
9. customto give 4.13 g (49%) of A2a as a yellow oil

ORD record

ord-bfbd3ea29b2a409c986c9d80f6b479ca

Source dataset

uspto-grants-2011_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08012963B2