Selectfluor → HCID 68802933, compound

HRID 1270752Notes

Reaction equation

HRID 1270752 reaction equation
[CH2:1]([O:3][C:4](=[O:17])[NH:5][C:6]1[C:15]([F:16])=[CH:14][C:13]2[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=2)[CH:7]=1)[CH3:2].[B-](F)(F)(F)[F:19].[B-](F)(F)(F)F.C1[N+]2(CCl)CC[N+](F)(CC2)C1>FC(F)(F)C(O)=O>[CH2:1]([O:3][C:4](=[O:17])[NH:5][C:6]1[C:15]([F:16])=[CH:14][C:13]2[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=2)[C:7]=1[F:19])[CH3:2]

Participants

4

Reactant 2

HCID 2724933SelectfluorHCID 68804849HCID 68804849, compound

Product 1

HCID 68802933HCID 68802933, compound

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Conditions

Temperature
70 °C

Procedure

A mixture of 1.63 g (7 mmol) of N-(3-fluoro-2-naphthyl)carbamic acid ethyl ester, and 2.73 g of Selectfluor® (7.7 mmol) in 10 mL of trifluoroacetic acid is heated to 70° C. under an atmosphere of nitrogen for 4 hours. After cooling to room temperature, the mixture is concentrated in vacuo and 30 mL of ice water is added. The mixture is extracted 3 times with 40 mL of CH2Cl2. The combined organic layers are washed with 40 mL each of H2O, saturated aqueous NaHCO3, saturated brine, dried over MgSO4. Evaporation of the solvents gives a residue that is purified by flash chromatography on silica gel (50% CH2Cl2/hexane) to give N-(1,3-difluoro-2-naphthyl)carbamic acid ethyl ester, which is hydrolyzed to 1,3-difluoro-2-aminonaphthalene under conditions described above.

Workup

  1. temperatureAfter cooling to room temperature
  2. concentrationthe mixture is concentrated in vacuo and 30 mL of ice water
  3. additionis added
  4. extractionThe mixture is extracted 3 times with 40 mL of CH2Cl2
  5. washThe combined organic layers are washed with 40 mL each of H2O, saturated aqueous NaHCO3, saturated brine
  6. dry with materialdried over MgSO4
  7. customEvaporation of the solvents
  8. customgives a residue that
  9. customis purified by flash chromatography on silica gel (50% CH2Cl2/hexane)

Sources & evidence

ORD record
ord-8aa8436283784c269ee6e0e1a145b331
Source dataset
uspto-grants-2007_04
Patent number
US07202364B2

Reaction notes

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