Tetrahydrofuran → HCID 66858248, compound

Participants

Reaction Steps

Step AAM (1): 2-(4-(Trifluoromethylthio)phenyl)acetic acid (4.7 g, 19.9 mmol) was deprotonated with NaHMDS 2.0 M in THF (19.9 mL, 39.8 mmol) and reacted with 1-chloro-4-iodobutane (2.44 mL, 19.9 mmol) using a procedure analogous to Step AC (1) to afford 6-chloro-2-(4-(trifluoromethylthio)-phenyl)hexanoic acid (3.07 g, 9.40 mmol, 47% yield) as a pale-yellow oil. LC-MS (M−H)− 325.2. 1H NMR (500 MHz, CHLOROFORM-d) δ ppm 1.32-1.51 (m, 2 H) 1.69-1.87 (m, 3 H) 2.01-2.17 (m, 1 H) 3.49 (t, J=6.56 Hz, 2 H) 3.59 (t, J=7.63 Hz, 1 H) 7.36 (d, J=8.24 Hz, 2 H) 7.61 (d, J=8.24 Hz, 2 H).

Provenance & Evidence