1,2,3-Trifluoro-4-nitrobenzene → HCID 59386302, compound

HRID 424022Notes

Reaction equation

HRID 424022 reaction equation
[F:1][C:2]1[CH:8]=[C:7]([I:9])[CH:6]=[CH:5][C:3]=1[NH2:4].[Li+].C[Si]([N-][Si](C)(C)C)(C)C.F[C:21]1[C:26]([F:27])=[C:25]([F:28])[CH:24]=[CH:23][C:22]=1[N+:29]([O-:31])=[O:30]>C1COCC1>[F:27][C:26]1[C:25]([F:28])=[CH:24][CH:23]=[C:22]([N+:29]([O-:31])=[O:30])[C:21]=1[NH:4][C:3]1[CH:5]=[CH:6][C:7]([I:9])=[CH:8][C:2]=1[F:1]

Participants

5

Reactant 3

HCID 698711,2,3-Trifluoro-4-nitrobenzeneHCID 1856942-Fluoro-4-iodoanilineHCID 2733832Lithium Hexamethyldisilazide

Product 1

HCID 59386302HCID 59386302, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent3×

Procedure

To a solution of 2-fluoro-4-iodoaniline (11.40 g, 47 mmol) in 100 ml anhydrous THF at 0° C., 47 ml of a 1M solution of LHMDS in THF (47 mmol) was added dropwise. The color of the solution turned dark purple. The solution was transferred via cannula to a dropping funnel, and the solution (containing the amine free base) was added in small portions to a solution of 2,3,4-trifluoronitrobenzene (8.321 g, 47.0 mmol) in anhydrous THF (50 ml) at 0° C. After completion of addition the mixture was stirred under argon at room temperature for 15 hours. The volume of the solvent was reduced, followed by extraction using ethyl acetate and brine. The organic layer was dried over sodium sulfate, the solvent was removed, and the obtained dark oil was purified by flash chromatography (EtOAc/hexane 1:5, Rf=0.58) yielding the crude product, which became a brown solid upon drying in vacuo (yield: 6.23 g, 33.6%). m/z=393 [M−1]−.

Workup

  1. customThe solution was transferred via cannula to a dropping funnel
  2. additionAfter completion of addition the mixture
  3. extractionfollowed by extraction
  4. dry with materialThe organic layer was dried over sodium sulfate
  5. customthe solvent was removed
  6. customthe obtained dark oil was purified by flash chromatography (EtOAc/hexane 1:5, Rf=0.58)

Sources & evidence

ORD record
ord-d9b205b02dc2420aa909be1f7525cdcd
Source dataset
uspto-grants-2012_01
Patent number
US08101799B2

Reaction notes

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