Nitric Acid → HCID 19800071, compound

HRID 1646879Notes

Reaction equation

HRID 1646879 reaction equation
[N+:1]([O-:4])(O)=[O:2].[Br:5][C:6]1[C:7]2[CH:14]=[C:13]([F:15])[CH:12]=[CH:11][C:8]=2[S:9][CH:10]=1.C(OC(=O)C)(=O)C>C(O)(=O)C>[Br:5][C:6]1[C:7]2[CH:14]=[C:13]([F:15])[CH:12]=[CH:11][C:8]=2[S:9][C:10]=1[N+:1]([O-:4])=[O:2]

Participants

5

Reactant 3

HCID 944Nitric AcidHCID 7918Acetic AnhydrideHCID 19800079138993-21-2

Product 1

HCID 19800071HCID 19800071, compoundYield 26%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A solution of 5.12 ml of fuming nitric acid and 4.5 ml of acetic acid was added dropwise, with stirring, to a cooled (5°-10° C.) mixture of 3-bromo-5-fluorobenzo[b]thiophene (5.35 g, 23.15 mmol) and 28.5 ml of acetic anhydride. The reaction mixture was stirred for 2 hours and poured onto ice water (350 ml) and extracted with CH2Cl2 (4×50 ml). The organic phases were combined, washed with water and dried over MgSO4. The solvent was evaporated and the residue was recrystallized from 90% ethanol to yield 1.7 g (26%) of 3-bromo-5-fluoro-2-nitrobenzo[b]thiophene. M.p. 129°-130° C. 1H-NMR(CDCl3): δ7.40 (ddd, 1H), 7.68 (ddd, 1H), 7.78 (dd, 1H).

Workup

  1. temperatureto a cooled
  2. stirringThe reaction mixture was stirred for 2 hours
  3. additionpoured onto ice water (350 ml)
  4. extractionextracted with CH2Cl2 (4×50 ml)
  5. washwashed with water
  6. dry with materialdried over MgSO4
  7. customThe solvent was evaporated
  8. customthe residue was recrystallized from 90% ethanol

Sources & evidence

ORD record
ord-e3d9178507be4b628ec0cadf935d8313
Source dataset
uspto-grants-1993_01
Patent number
US05182279

Reaction notes

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