Stannous Chloride → HCID 59609202, 화합물

HRID 405043

반응식

HRID 405043 반응식
[Mg].[CH2:2]([CH:4]([CH2:7][CH2:8][CH2:9][CH3:10])[CH2:5]Br)[CH3:3].[S:11]1[CH:15]=[CH:14][C:13]2[C:16](=O)[C:17]3[S:18][CH:19]=[CH:20][C:21]=3[C:22](=O)[C:12]1=2.Cl[Sn]Cl>[Cl-].[Na+].O.C1COCC1>[CH2:2]([CH:4]([CH2:7][CH2:8][CH2:9][CH3:10])[CH2:5][C:16]1[C:17]2[S:18][CH:19]=[CH:20][C:21]=2[C:22]([CH2:5][CH:4]([CH2:2][CH3:3])[CH2:7][CH2:8][CH2:9][CH3:10])=[C:12]2[S:11][CH:15]=[CH:14][C:13]=12)[CH3:3]

참가 물질

7

반응물 4

HCID 24479Stannous ChlorideHCID 868042-Ethylhexyl bromideHCID 288478(Benzo(1,2-b:4,5-b)dithiophene-4,8-dione)HCID 5462224Magnesium2회

생성물 1

HCID 59609202HCID 59609202, 화합물수율 43%

시약·촉매·용매 2

HCID 8028Tetrahydrofuran용매HCID 57417360Sodium chloride; water용매

실험 절차

To a 100 mL flask under nitrogen was added magnesium (656 mg, 27 mmol) and anhydrous THF (10 mL). The mixture was heated under reflux and 2-ethylhexyl bromide (5.6 mL, mmol) was added dropwise. The reaction mixture was kept at refluxing temperatures until all magnesium was consumed. After cooling down, 4,8-dihydrobenzo[1,2-b:4,5-b′]dithiophene-4,8-dione (1.1 g, 5.0 mmol) was added in one portion. After refluxing for 1 hour more, it was cooled down again to room temperature. SnCl2 solution (7.5 g in 19 mL 10% HCl) was slowly added dropwise and then the mixture was kept at 60° C. for 1 hour. After cooling down, brine (11 mL) was added. The organic phase was separated and dried over Na2SO4. The residue after vacuum evaporation was purified by column chromatography with hexane as eluent and gave a pale yellow oil (910 mg, yield 43%). 1H NMR (CDCl3, 500 MHz) δ=7.47 (d, J=6.0 Hz, 2H), 7.45 (d, J=6.0 Hz, 2H), 3.08-3.20 (m, 4H), 1.92-2.04 (m, 2H), 1.13-1.49 (m, 16H), 0.91 (t, J=7.0 Hz, 6H), 0.85 (t, J=7.0 Hz, 6H).

후처리

  1. temperatureThe mixture was heated
  2. temperatureunder reflux
  3. customwas consumed
  4. temperatureAfter cooling down
  5. temperatureAfter refluxing for 1 hour more
  6. temperatureAfter cooling down
  7. customThe organic phase was separated
  8. dry with materialdried over Na2SO4
  9. customThe residue after vacuum evaporation
  10. customwas purified by column chromatography with hexane as eluent

출처 및 근거

ORD 기록
ord-f3a71e268aec4b88b46f935d0865b0c8
출처 데이터셋
uspto-grants-2014_06
특허 번호
US08748739B2

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