Acetic Acid → Thieno(2,3-b)thiophene, 3,4-dibromo-

HRID 1640328노트

반응식

HRID 1640328 반응식
Br[C:2]1[S:11][C:5]2[S:6][C:7](Br)=[C:8]([Br:9])[C:4]=2[C:3]=1[Br:12].C(O)(=O)C>[Zn].O>[Br:9][C:8]1[C:4]2[C:3]([Br:12])=[CH:2][S:11][C:5]=2[S:6][CH:7]=1

참가 물질

5

반응물 2

HCID 176Acetic AcidHCID 143033Thieno(2,3-b)thiophene, 2,3,4,5-tetrabromo-

생성물 1

HCID 143030Thieno(2,3-b)thiophene, 3,4-dibromo-수율 72.5%

시약·촉매·용매 2

HCID 23994Zinc촉매HCID 962Water용매

실험 절차

A mixture of 2,3,4,5-tetrabromothieno[2,3-b]thiophene (0.83 g, 1.8 mmol), zinc dust (0.29 g, 4.4 mmol), and acetic acid (30 ml) is refluxed for 2 h. The reaction mixture is poured into water, extracted with DCM, washed with aqueous saturated sodium carbonate solution, dried (Na2SO4), and concentrated under reduced pressure. The product is purified by recrystallisation from hot methanol to obtain white fibrous crystals (389 mg, 72%). M/Z (298, t, M+). Found C, 24.5; H, 0.8. Calc. for C6H2Br2S2C, 24.2; H, 0.7. 1H NMR (300 MHz, CDCl3) δ 7.32 (s, 2H). 13C NMR (300 MHz, CDCl3) δ 139.35, 137.42, 126.44, 102.96.

후처리

  1. temperatureis refluxed for 2 h
  2. extractionextracted with DCM
  3. washwashed with aqueous saturated sodium carbonate solution
  4. dry with materialdried (Na2SO4)
  5. concentrationconcentrated under reduced pressure
  6. customThe product is purified by recrystallisation from hot methanol

출처 및 근거

ORD 기록
ord-727fb6da539442389e9bf6d7b5bf3943
출처 데이터셋
uspto-grants-2012_02
특허 번호
US08114316B2

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