Tetrahydrothiophene → 1-[2-(Naphthalen-2-yl)-2-oxoethyl]thiolan-1-ium bromide

HRID 1662924Notes

Reaction equation

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

Participants

Conditions

Temperature: 0 °C

Procedure

To a solution of 2-bromo-2′-acetonaphthone (18.68 g, 75 mmol) in 100 mL of acetone and 4.1 mL of water at 0° C. was added tetrahydrothiophene (13.23 g, 150 mmol) dropwise. The resulting mixture was stirred at 0° C. for 1 hour before solid precipitated and was then stirred at room temperature for 1 hour. The resulting crude product was filtered through glass frit as solid and was washed by 100 mL of cold acetone. The crude product was recrystallized by 150 mL of ethanol to afford 19.0 g pure product at a yield of 75%. 1HNMR, d6-DMSO: 8.82 (s, 1H), 8.17-7.98 (m, 4H), 7.78-7.65 (m, 2H), 5.63 (s, 2H), 3.64 (m, 4H), 2.40-2.29 (brm, 2h), 2.28-2.17 (brm, 2H).

Workup

customprecipitated
stirringwas then stirred at room temperature for 1 hour
filtrationThe resulting crude product was filtered through glass frit as solid
washwas washed by 100 mL of cold acetone
customThe crude product was recrystallized by 150 mL of ethanol

Sources & evidence

ORD record: ord-a635186052ac4a2696f48852fe9245c6
Source dataset: uspto-grants-2011_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08034533B2

Reaction notes

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