Diethyl Ether → HCID 18966284, compound

HRID 2226099Notes

Reaction equation

HRID 2226099 reaction equation
FC(F)(F)C(O)=O.[CH3:8][C:9]1([CH3:27])[O:13][C:12]2[CH:14]=[CH:15][C:16]([F:26])=[C:17]([NH:18]C(=O)OC(C)(C)C)[C:11]=2[O:10]1.C(OCC)C.C(=O)(O)[O-].[Na+]>O>[NH2:18][C:17]1[C:11]2[O:10][C:9]([CH3:8])([CH3:27])[O:13][C:12]=2[CH:14]=[CH:15][C:16]=1[F:26]

Participants

6

Reactant 4

HCID 3283Diethyl EtherHCID 6422Trifluoroacetic acid2×HCID 516892Sodium BicarbonateHCID 18966278HCID 18966278, compound

Product 1

HCID 18966284HCID 18966284, compoundYield 65.2%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

In a flask was placed 50 mL of trifluoroacetic acid which was cooled to 0° C. To this cooled trifluoroacetic acid was added 11.5 g (0.041 mole) of t-butyl N-(2,2-dimethyl-5-fluoro-1,3-benzodioxol-4-yl)carbamate. This mixture was allowed to warm to ambient temperature at which it was stirred for 90 minutes. Diethyl ether and water were added to the mixture which was made basic with sodium bicarbonate. The organic phase was separated from the aqueous phase, and the former was dried with anhydrous magnesium sulfate and filtered. The filtrate was concentrated under reduced pressure, and the residue was passed through a column of silica gel, eluting with methylene chloride/heptane (1:1). Product-containing fractions were combined and the solvent evaporated under reduced pressure, yielding 4.9 g of 4-amino-2,2-dimethyl-5-fluoro-1,3-benzodioxole as the residue. The NMR spectrum was consistent with the proposed structure.

Workup

  1. customIn a flask was placed
  2. customThe organic phase was separated from the aqueous phase
  3. dry with materialthe former was dried with anhydrous magnesium sulfate
  4. filtrationfiltered
  5. concentrationThe filtrate was concentrated under reduced pressure
  6. washeluting with methylene chloride/heptane (1:1)
  7. customthe solvent evaporated under reduced pressure

Sources & evidence

ORD record
ord-adaf36e45964446f8bbf4c1af5b96f6d
Source dataset
uspto-grants-1994_09
Patent number
US05346881

Reaction notes

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