Tetrafluoroboric acid → HCID 66767144, compound

HRID 1662001Notes

Reaction equation

HRID 1662001 reaction equation
[Br:1][C:2]1[CH:17]=[CH:16][C:5]([O:6][C:7]2[C:13]([F:14])=[CH:12][C:10]([NH2:11])=[C:9]([CH3:15])[CH:8]=2)=[C:4]([F:18])[CH:3]=1.F[B-](F)(F)F.[H+].[N:25]([O-])=O.[Na+].CC([O-])=O.[K+].C1OCCOCCOCCOCCOCCOC1>O.C(Cl)(Cl)Cl>[Br:1][C:2]1[CH:17]=[CH:16][C:5]([O:6][C:7]2[CH:8]=[C:9]3[C:10](=[CH:12][C:13]=2[F:14])[NH:11][N:25]=[CH:15]3)=[C:4]([F:18])[CH:3]=1

Participants

8

Reactant 5

HCID 28118Tetrafluoroboric acidHCID 2855718-Crown-6HCID 517044Potassium AcetateHCID 23668193Sodium NitriteHCID 66766834HCID 66766834, compound

Product 1

HCID 66767144HCID 66767144, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 6212ChloroformSolvent

Conditions

Temperature
0 °C

Procedure

To a suspension of 4-(4-bromo-2-fluorophenoxy)-5-fluoro-2-methylaniline (5.2 g, 16.6 mmol) in water (100 mL) is added fluoroboric acid (6.06 g, 33.1 mmol) at RT. The solution is cooled to 0° C. and NaNO2 (1.71 g, 24.8 mmol) in water (2 mL) is added. The reaction is stirred at 0° C. for 40 min. CHCl3 (200 mL) is added. The organic phase is separated, dried over Na2SO4, and filtered. To the filtrate is added KOAc (7.31 g, 74.5 mmol) and 18-crown-6-ether (0.218 g, 0.82 mmol). The reaction is stirred at RT for 1 hour. The reaction mixture is washed with saturated aqueous sodium chloride, dried over Na2SO4, filtered and evaporated. The residue is washed with DCM and filtered to offer the desired product as a light yellow solid. The filtrate is purified by chromatography eluting with DCM then EtOAc:hexane (1:1) to give additional desired product. Both portions of the solid are combined to offer the desired product (3.2 g, 59% yield). MS (m/z): 324.8 (M+H).

Workup

  1. customThe organic phase is separated
  2. dry with materialdried over Na2SO4
  3. filtrationfiltered
  4. stirringThe reaction is stirred at RT for 1 hour
  5. washThe reaction mixture is washed with saturated aqueous sodium chloride
  6. dry with materialdried over Na2SO4
  7. filtrationfiltered
  8. customevaporated
  9. washThe residue is washed with DCM
  10. filtrationfiltered
  11. customThe filtrate is purified by chromatography
  12. washeluting with DCM

Sources & evidence

ORD record
ord-5d78d07b73354c72976d0639c6853ea8
Source dataset
uspto-grants-2011_10
Patent number
US08030302B2

Reaction notes

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