Dimethylformamide → HCID 17986946, compound

Temperature

0 °C

To a solution of 4-(4-fluorophenyl)-butyric acid (6.7 g) in chloroform (15 ml) at 0° C. was added 0.1 ml DMF followed by the addition of oxalyl chloride (3.35 ml) over 20 min. The solution was stirred for 2 h then concentrated. The crude acid chloride was dissolved in chloroform (150 ml) and cooled to 0° C., whereupon concentrated ammonia solution (6 ml) was added over 15 min and the resulting solution stirred for 2 h. The reaction mixture was washed with water and the organic phase dried (MgSO4) and concentrated in vacuo. The crude product was chromatographed over silica using a gradient elution from ether to 2:1 acetone/ether to yield the title compound (2.86 g, 43%). 1H-NMR (CDCl3) δ 1.96 (2H, app q), 2.21 (2H, t), 2.65 (2H, t), 5.41 (2H, br s), 6.96 (2H, m), 7.14 (2H, m). MS (APCI+) M+1=182, C10H12FNO requires 181.

1. concentrationthen concentrated
2. dissolutionThe crude acid chloride was dissolved in chloroform (150 ml)
3. additionwas added over 15 min
4. stirringthe resulting solution stirred for 2 h
5. washThe reaction mixture was washed with water
6. dry with materialthe organic phase dried (MgSO4)
7. concentrationconcentrated in vacuo
8. customThe crude product was chromatographed over silica using
9. washa gradient elution from ether to 2:1 acetone/ether

ORD record

ord-c0810d63930a4f53bb9130117a427eb2

Source dataset

uspto-grants-2008_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07462620B2