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Ethanol → 7-Bromo-5-fluoro-1-benzofuran

HRID 1371744
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HRID 1371744 반응식
[Br:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[O:9][CH2:10][CH:11](OCC)OCC.C(O)C>ClC1C=CC=CC=1>[Br:1][C:2]1[C:3]2[O:9][CH:10]=[CH:11][C:4]=2[CH:5]=[C:6]([F:8])[CH:7]=1
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참가 물질

4

반응물 2

HCID 702EthanolHCID 22144836HCID 22144836, 화합물

생성물 1

HCID 221448167-Bromo-5-fluoro-1-benzofuran수율 33%

시약·촉매·용매 1

HCID 7964Chlorobenzene용매2회

실험 절차

2-Bromo-1-(2,2-diethoxy-ethoxy)-4-fluoro-benzene (60 g, 0.22 mol, Step A) was combined with Amberlyst-15 (20 g, Aldrich) in chlorobenzene (500 mL, Aldrich) and stirred with a paddle stirrer while the temperature was maintained at very gentle reflux. At the same time an azeotrope containing ethanol and chlorobenzene was removed via downward distillation. After 2 hours, more chlorobenzene was added (200 mL) and additional azeotrope was collected. The content of the flask was filtered and excess chlorobenzene was distilled (45° C., at ˜1 mm). The residue was purified by silica gel chromatography (5–10% ethyl ether/hexane) to give 7-bromo-5-fluoro-benzofuran (14 g, ˜33%) and taken to the next step. H1NMR (300 MHz, DMSOd6), ppm: 8.20 (d), 1H, 7.52 (m), 2H, 7.10 (d), 1H.

후처리

  1. temperaturewas maintained at very gentle reflux
  2. customwas removed via downward distillation
  3. additionmore chlorobenzene was added (200 mL) and additional azeotrope
  4. customwas collected
  5. filtrationThe content of the flask was filtered
  6. distillationexcess chlorobenzene was distilled (45° C., at ˜1 mm)
  7. customThe residue was purified by silica gel chromatography (5–10% ethyl ether/hexane)

출처 및 근거

ORD 기록
ord-ed2b9230f1424e4abaa8bdd2be6c5379
출처 데이터셋
uspto-grants-2007_01
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07157455B2

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