Hydrochloric Acid → 2-Thiopenecarboxaldehyde, 3,4,5-trichloro-

HRID 374514Notes

Reaction equation

C([Li])CCC.[Cl:6][C:7]1[S:11][C:10](Cl)=[C:9]([Cl:13])[C:8]=1[Cl:14].CN(C)[CH:17]=[O:18].Cl>O1CCCC1.CCCCCC.C(OCC)(=O)C>[Cl:13][C:9]1[C:8]([Cl:14])=[C:7]([Cl:6])[S:11][C:10]=1[CH:17]=[O:18]

Participants

Conditions

Temperature: 0 °C

Procedure

Butyllithium (2.5 molar in tetrahydrofuran, 3.96 mL, 9.9 mmol) is added to a solution of tetrachlorothiophene (2.00 g, 9.01 mmol) in tetrahydrofuran at 0° C. The reaction mixture is stirred at 0° C. for 30 minutes, warmed to room temperature over 45 minutes, treated with N,N-dimethylformamide (0.79 g, 10.8 mmol), stirred for three hours, poured into one molar hydrochloric acid at 4° C. and extracted with ether. The combined organic extracts are washed sequentially with water and brine, dried over MgSO4 and concentrated in vacuo to obtain a brown solid. Flash chromatography of the solid using silica gel and a 5% ethyl acetate in hexane solution gives a beige solid which is recrystallized from ethyl acetate and hexane to obtain the title product as beige needles (1.63 g, 84%, mp 81°-82° C.).

Workup

temperaturewarmed to room temperature over 45 minutes
stirringstirred for three hours
extractionextracted with ether
washThe combined organic extracts are washed sequentially with water and brine
dry with materialdried over MgSO4
concentrationconcentrated in vacuo
customto obtain a brown solid
customis recrystallized from ethyl acetate and hexane

Sources & evidence

ORD record: ord-5f224ebb82a945a08c08fe2453113b7d
Source dataset: uspto-grants-1996_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05480902

Reaction notes

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