2-Fluoro-4-iodoaniline → HCID 57624947, compound

HRID 881647Notes

Reaction equation

HRID 881647 reaction equation
F[C:2]1[CH:9]=[C:8]([F:10])[CH:7]=[C:6]([F:11])[C:3]=1[C:4]#[N:5].[F:12][C:13]1[CH:18]=[C:17]([I:19])[CH:16]=[CH:15][C:14]=1[NH2:20].CC(C)([O-])C.[K+]>C1COCC1>[F:11][C:6]1[CH:7]=[C:8]([F:10])[CH:9]=[C:2]([NH:20][C:14]2[CH:15]=[CH:16][C:17]([I:19])=[CH:18][C:13]=2[F:12])[C:3]=1[C:4]#[N:5]

Participants

5

Reactant 3

HCID 1856942-Fluoro-4-iodoanilineHCID 7371772,4,6-TrifluorobenzonitrileHCID 23665647Potassium tert-butoxide

Product 1

HCID 57624947HCID 57624947, compoundYield 173.7%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-65 °C

Procedure

In analogy to GP 1, 1 g of 2,4,6-trifluoro-benzonitrile (6.37 mmol; 1 eq.; commercially available) and 2.26 g 2-fluoro-4-iodo-benzenamine (9.55 mmol, 1.5 eq; commercially available) were dissolved in 100 ml of THF. The mixture was cooled to −65° C.; 2.14 g of potassium tert-butoxide (19.1 mmol, 3 eq; commercially available) were added. The mixture was stirred for 35 min at this temperature and another 21 h at RT. The mixture was stirred into 120 ml of ice water and extracted three times with ethyl acetate (100 ml each). The combined organic layers were washed with brine, dryed over sodium sulfate and concentrated to afford 4.137 g of crude product. Purification was achieved by flash chromatography (hexane/ethyl acetate) to afford 646 mg (27.13% yield; 1.73 mmol) of the target compound.

Workup

  1. additioncommercially available) were added
  2. extractionextracted three times with ethyl acetate (100 ml each)
  3. washThe combined organic layers were washed with brine
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-69e041f99d0f4cd19e1525ddb72bf523
Source dataset
uspto-grants-2015_03
Patent number
US08993630B2

Reaction notes

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