Boron trifluoride → (4,5-Difluoro-7-nitro-benzofuran-6-yl)-(2-fluoro-4-iodo-phenyl)-amine

HRID 1261395

Reaktionsgleichung

Reaktionsgleichung von HRID 1261395
C(O[CH:4](OCC)[CH2:5][O:6][C:7]1[C:8]([N+:24]([O-:26])=[O:25])=[C:9]([C:19]([F:23])=[C:20]([F:22])[CH:21]=1)[NH:10][C:11]1[CH:16]=[CH:15][C:14]([I:17])=[CH:13][C:12]=1[F:18])C.B(F)(F)F>C(Cl)Cl>[F:22][C:20]1[C:21]2[CH:4]=[CH:5][O:6][C:7]=2[C:8]([N+:24]([O-:26])=[O:25])=[C:9]([NH:10][C:11]2[CH:16]=[CH:15][C:14]([I:17])=[CH:13][C:12]=2[F:18])[C:19]=1[F:23]

Komponenten

4

Edukt 2

HCID 6356Boron trifluorideHCID 866714883-(2,2-Diethoxyethoxy)-5,6-difluoro-N-(2-fluoro-4-iodophenyl)-2-nitroaniline

Produkt 1

HCID 67235416(4,5-Difluoro-7-nitro-benzofuran-6-yl)-(2-fluoro-4-iodo-phenyl)-amineAusbeute 69,5 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel2×

Versuchsvorschrift

For scale up, a solution of 3-(2,2-diethoxyethoxy)-5,6-difluoro-N-(2-fluoro-4-iodophenyl)-2-nitroaniline (75 g) in 300 mL of DCM was added quickly into a solution of BF3.ET2O in 100 mL of DCM at 28-32° C. with further stirring for 15 minutes. After about 2 hours, analysis showed complete conversion. The solution was then quenched by 1N NaOH (dropwise) at a temperature below 30° C. to pH 10 before separating. DCM was then washed with water twice to a pH of about 7 and concentrated to dryness. 210 mL of MBTE was then added. The suspension was stirred for 30 minutes, filtered and dried to give 43 g of an orange solid. 1H NMR (CDCl3, 400 MHz): δ 8.80 (bs, 1H), 7.75 (d, 1H), 7.48 (dd, 1H), 7.41 (d; 1H); 6.97 (d, 1H), 6.75-6.80 (m, 1H).

Aufarbeitung

  1. customThe solution was then quenched by 1N NaOH (dropwise) at a temperature below 30° C. to pH 10
  2. custombefore separating
  3. washDCM was then washed with water twice to a pH of about 7
  4. concentrationconcentrated to dryness
  5. addition210 mL of MBTE was then added
  6. filtrationfiltered
  7. customdried

Quellen und Nachweise

ORD-Eintrag
ord-fc3a9e148aff401695f59c03e0aef737
Quelldatensatz
uspto-grants-2013_06
Patentnummer
US08470878B2

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