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N-bromobutanimide → HCID 86730632, Verbindung

HRID 332851
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 332851
[F:1][C:2]1[C:7]2[S:8][C:9]([C:11]3[CH:16]=[CH:15][C:14]([O:17][CH3:18])=[CH:13][CH:12]=3)=[CH:10][C:6]=2[CH:5]=[CH:4][C:3]=1[O:19][CH3:20].[F:21][C:22]1[C:38]([O:39][CH3:40])=[C:37]([F:41])[C:25]2[S:26][C:27]([C:29]3[CH:34]=[CH:33][C:32]([O:35][CH3:36])=[CH:31][CH:30]=3)=[CH:28][C:24]=2[CH:23]=1.C1C(=O)N([Br:49])C(=O)C1>C1COCC1.C(Cl)Cl.[O-]S([O-])(=S)=O.[Na+].[Na+]>[Br:49][C:10]1[C:6]2[CH:5]=[CH:4][C:3]([O:19][CH3:20])=[C:2]([F:1])[C:7]=2[S:8][C:9]=1[C:11]1[CH:16]=[CH:15][C:14]([O:17][CH3:18])=[CH:13][CH:12]=1.[Br:49][C:28]1[C:24]2[CH:23]=[C:22]([F:21])[C:38]([O:39][CH3:40])=[C:37]([F:41])[C:25]=2[S:26][C:27]=1[C:29]1[CH:34]=[CH:33][C:32]([O:35][CH3:36])=[CH:31][CH:30]=1
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

8

Edukt 3

HCID 67184N-bromobutanimideHCID 86730634HCID 86730634, VerbindungHCID 86730635HCID 86730635, Verbindung

Produkt 2

HCID 86730632HCID 86730632, VerbindungAusbeute 43,6 %HCID 867306333-Bromo-5,7-difluoro-6-methoxy-2-(4-methoxyphenyl)benzo[b]thiopheneAusbeute 24,62 %

Reagenzien, Katalysatoren, Lösungsmittel

3
HCID 6344DichloromethaneLösungsmittelHCID 8028TetrahydrofuranLösungsmittelHCID 24477Sodium ThiosulfateLösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

To a round bottom flask, an unseparated mixture of 7-fluoro-6-methoxy-2-(4-methoxyphenyl)benzo[b]thiophene and 5,7-difluoro-6-methoxy-2-(4-methoxyphenyl)benzo[b]thiophene (380 mg, 1.318 mmol) was dissolved in THF (10 mL) and the solution was cooled to 0° C. To the solution was added NBS (237 mg, 1.331 mmol). The reaction mixture was stirred at 0° C. for 1 h then warmed to room temperature and stirred for an additional 2 h. The reaction mixture was concentrated to afford the crude product. The crude product was diluted with DCM and sat. Na2S2O3 (sodium thiosulfate). The organic layer was collected (phase separator) and concentrated. The reaction mixture was diluted with water and DCM. The organic phase was collected (phase separator) and concentrated to afford the crude product. The crude material was purified by column chromatography (SiO2, 0-5% Heptanes/EtOAc) to afford 3-bromo-7-fluoro-6-methoxy-2-(4-methoxyphenyl)benzo[b]thiophene (211 mg, 0.575 mmol, 43.6% yield) and 3-bromo-5,7-difluoro-6-methoxy-2-(4-methoxyphenyl)benzo[b]thiophene (125 mg, 0.324 mmol, 24.62% yield). 3-bromo-7-fluoro-6-methoxy-2-(4-methoxyphenyl)benzo[b]thiophene: 1H NMR (400 MHz, CDCl3) δ ppm=7.56-7.66 (m, 2H), 7.46 (dd, J=1.01, 8.59 Hz, 1H), 7.11 (dd, J=7.58, 8.59 Hz, 1H), 6.90-6.97 (m, 2H), 3.92 (s, 3H), 3.79 (s, 3H). 3-bromo-5,7-difluoro-6-methoxy-2-(4-methoxyphenyl)benzo[b]thiophene: 1H NMR (400 MHz, CDCl3) δ ppm=7.53-7.68 (m, 2H), 7.48 (d, J=8.59 Hz, 1H), 7.15-7.27 (m, 1H), 7.07 (dt, J=2.53, 8.59 Hz, 1H), 3.98 (s, 3H), 4.02 (s, 3H).

Aufarbeitung

  1. temperaturethen warmed to room temperature
  2. stirringstirred for an additional 2 h
  3. concentrationThe reaction mixture was concentrated
  4. customto afford the crude product
  5. customThe organic layer was collected (phase separator)
  6. concentrationconcentrated
  7. additionThe reaction mixture was diluted with water and DCM
  8. customThe organic phase was collected (phase separator)
  9. concentrationconcentrated
  10. customto afford the crude product
  11. customThe crude material was purified by column chromatography (SiO2, 0-5% Heptanes/EtOAc)

Quellen und Nachweise

ORD-Eintrag
ord-75a158d1e0564ccca05873a38e6d697b
Quelldatensatz
uspto-grants-2014_11
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08877801B2

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