Nitric Acid → 3-Bromo-2-nitro-benzo(b)thiophene

HRID 1350483

Reaktionsgleichung

Reaktionsgleichung von HRID 1350483
[N+:1]([O-:4])(O)=[O:2].[Br:5][C:6]1[C:7]2[CH:14]=[CH:13][CH:12]=[CH:11][C:8]=2[S:9][CH:10]=1>C(O)(C(F)(F)F)=O.ClCCl>[Br:5][C:6]1[C:7]2[CH:14]=[CH:13][CH:12]=[CH:11][C:8]=2[S:9][C:10]=1[N+:1]([O-:4])=[O:2]

Komponenten

5

Edukt 2

HCID 944Nitric AcidHCID 123250Benzo(b)thiophene, 3-bromo-

Produkt 1

HCID 2970503-Bromo-2-nitro-benzo(b)thiophene

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6344DichloromethaneLösungsmittel2×HCID 6422Trifluoroacetic acidLösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

Add dropwise fuming nitric acid(90%, 8.6 mL, 183 mmol) to a mixture of 3-bromo benzo[b]thiophene (39g, 183 mmol) in TFA(100 mL) and dichloromethane (400mL) at 0° C. The reaction turn greenish, then yellow precipitates. To this reaction mixture, add dichloromethane (200 mL) and the reaction stir at 0° C. for 30 min. Then pour the reaction into ice-water (2 L). Extract with dichloromethane (3×500mL) and the organic layer dry over MgSO4. Evaporation give a yellow solid. The resulting yellow solid triturate with diethyl ether to give a yellow solid. (Total: 34.8 g, 73%). Mass spectrum (m/e): 259 (M+1); 1HNMR(300 MHz, DMSO-d6) δ ppm: 7.70 (tt, 2H), 8.04 (d, 1H), 8.17 (d, 1H). 3CNMR(75 MHz, DMSO-d6) δ ppm: 112.5, 124.8, 126.9, 127.9, 131.3, 137.0, 137.2, 166.1.

Aufarbeitung

  1. additionThen pour
  2. extractionExtract with dichloromethane (3×500mL)
  3. dry with materialthe organic layer dry over MgSO4
  4. customEvaporation
  5. customgive a yellow solid
  6. customThe resulting yellow solid triturate with diethyl ether
  7. customto give a yellow solid

Quellen und Nachweise

ORD-Eintrag
ord-eccca73f9ebe4665bc4f4c51215be896
Quelldatensatz
uspto-grants-2007_05
Patentnummer
US07214673B2

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