Tetrahydrothiophene → HCID 86604150, compound

HRID 2356199Notes

Reaction equation

[S:1]1[CH2:5][CH2:4][CH2:3][CH2:2]1.[F:6][C:7]([F:23])([F:22])[C:8]1[CH:13]=[C:12]([CH2:14][Br:15])[C:11]([C:16]([F:19])([F:18])[F:17])=[CH:10][C:9]=1[CH2:20]Br>CO>[Br-:15].[Br-:15].[F:6][C:7]([F:23])([F:22])[C:8]1[CH:13]=[C:12]([CH2:14][S+:1]2[CH2:5][CH2:4][CH2:3][CH2:2]2)[C:11]([C:16]([F:19])([F:18])[F:17])=[CH:10][C:9]=1[CH2:20][S+:1]1[CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

Conditions

Temperature: 50 °C

Procedure

Tetrahydrothiophene (0.27 mL, 3 mmol) was added to a suspension of compound 24 (200 mg, 0.5 mmol) in dry methanol (5 mL). The solid was dissolved to form a clear solution within 10 min. This solution was filtered via 0.45 μm membrane filter and then heated to 50° C. with stirring for 24 h. After cooling down to room temperature, the solvent was completely removed in vacuo and cold acetone (10 mL) was added to the residue. The precipitate was then filtered and dried to give compound 217a as a colorless, hygroscopic solid (192 mg, 67%): 1H NMR (300 MHz, D2O): 8.17 (2H, s), 4.76 (4H, s), 3.52-3.62 (8H, m), 2.34-2.47 (8H, m); 19F NMR (282 MHz, D2O): −60.2; HR-MS (EI) calcd. for C18H22F6S2Br2 (M+): 573.94, found ([M-Br]+): 495.04.

Workup

dissolutionThe solid was dissolved
customto form a clear solution within 10 min
filtrationThis solution was filtered via 0.45 μm membrane
filtrationfilter
temperatureAfter cooling down to room temperature
customthe solvent was completely removed in vacuo and cold acetone (10 mL)
additionwas added to the residue
filtrationThe precipitate was then filtered
customdried

Sources & evidence

ORD record: ord-5fcb0f356f6b4421be5c0e8843522cc6
Source dataset: uspto-grants-2010_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07759127B2

Reaction notes

Loading…