Dimethyl Sulfoxide → 2-(3-Fluorophenyl)propanal

Anhydrous CH2Cl2 (10 mL) was cooled to −78° C., and anhydrous DMSO (0.546 g, 7.00 mmol) was added, followed, dropwise, by oxalyl chloride (0.380 g, 3.00 mmol). Once gas evolution ceased, compound 40 (0.308 g, 2 mmol) was added dropwise and the resulting milky solution was stirred for 15 min. Et3N (1.17 mL, 8.4 mmol) was added slowly and the mixture was stirred for 15 min at −78° C. and then warmed to room temperature and stirred for 1 h. The yellow mixture was diluted with H2O (30 mL) and the layers were separated. The aqueous layer was extracted with CH2Cl2 (2×15 mL), and the organic layers were washed with H2O and sat. aq. NaCl (15 mL each). The solution was dried over anhydrous sodium sulfate, concentrated, and the resulting residue was purified by flash column chromatography (SiO2), eluting with a gradient of hexanes to 10% EtOAc in hexanes to yield the title aldehyde as a colorless volatile oil (0.220 g, 72%). 1H-NMR (500 MHz; CDCl3): δ 9.82 (s, 1 H), 7.27-7.23 (m, 1 H), 6.97 (d, J=7.6 Hz, 1 H), 6.92-6.89 (m, 2 H), 2.96 (t, J=7.5 Hz, 2 H), 2.81-2.78 (m, 2 H).

1. stirringthe mixture was stirred for 15 min at −78° C.
2. stirringstirred for 1 h
3. customthe layers were separated
4. extractionThe aqueous layer was extracted with CH2Cl2 (2×15 mL)
5. washthe organic layers were washed with H2O and sat. aq. NaCl (15 mL each)
6. dry with materialThe solution was dried over anhydrous sodium sulfate
7. concentrationconcentrated
8. customthe resulting residue was purified by flash column chromatography (SiO2)
9. washeluting with a gradient of hexanes to 10% EtOAc in hexanes

ORD record

ord-22910ea5d1bc43b4860e9cdd2155461f

Source dataset

uspto-grants-2015_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09212144B2