2-(4-Fluorophenyl)acetic acid → HCID 58110139, compound

Temperature

0 °C

Step AAI (4): NaHMDS 2.0 M in THF (11.0 mL, 21.9 mmol) was added to a solution of 2-(4-fluorophenyl)acetic acid (1.50 g, 9.73 mmol) in THF (19.5 mL) at 0° C. The resulting mixture was stirred for 20 min at 0° C., then neat 2-(bromomethyl)-4-chlorobut-1-ene (1.96 g, 10.7 mmol) was added. After 10 min, the mixture was quenched with a water (5 mL) and concentrated in vacuo. The mixture was diluted with EtOAc and the organic layer was washed with 1N HCl, then brine, dried over sodium sulfate, and concentrated in vacuo to afford 5-(chloromethyl)-2-(4-fluorophenyl)hex-5-enoic acid. The titled product was used for subsequent chemistry without further purification. LC-MS (M−H)− 255.1. 1H NMR (500 MHz, CHLOROFORM-d) δ ppm 7.24-7.41 (2 H, m), 6.96-7.11 (2 H, m), 4.91 (2 H, d, J=3.1 Hz), 3.82 (1 H, dd, J=8.7, 6.9 Hz), 3.60 (2 H, t, J=7.2 Hz), 2.84 (1 H, dd, J=15.0, 8.9 Hz), 2.39-2.55 (3 H, m).

1. waitAfter 10 min
2. customthe mixture was quenched with a water (5 mL)
3. concentrationconcentrated in vacuo
4. additionThe mixture was diluted with EtOAc
5. washthe organic layer was washed with 1N HCl
6. dry with materialbrine, dried over sodium sulfate
7. concentrationconcentrated in vacuo

ORD record

ord-581462fa46be4790b9bb2d87160fa753

Source dataset

uspto-grants-2013_01

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08349880B2