Trifluoroacetic acid → 3-Ethoxy-2,6-difluoroaniline

HRID 459949Notes

Reaction equation

HRID 459949 reaction equation
C(OC(=O)[NH:7][C:8]1[C:13]([F:14])=[CH:12][CH:11]=[C:10]([O:15][CH2:16][CH3:17])[C:9]=1[F:18])(C)(C)C.FC(F)(F)C(O)=O>ClCCl>[CH2:16]([O:15][C:10]1[C:9]([F:18])=[C:8]([NH2:7])[C:13]([F:14])=[CH:12][CH:11]=1)[CH3:17]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 69028840(3-Ethoxy-2,6-difluoro-phenyl)-carbamic acid tert-butyl ester

Product 1

HCID 184447123-Ethoxy-2,6-difluoroanilineYield 71.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of (3-ethoxy-2,6-difluoro-phenyl)-carbamic acid tert-butyl ester (135 g, 0.525 mol) in a mixture of dichloromethane and 10 equivalents trifluoroacetic acid (598 g, 5.25 mol) was stirred at room temperature for 1 hour and concentrated in vacuo. The pH of the residue was adjusted to pH 8 with a saturated aqueous solution of sodium bicarbonate. The organic layer was separated and the aqueous layer is extracted with ethyl acetate (3×250 mL). The organic extracts were combined, washed with a saturated aqueous solution of sodium chloride (2×), dried and concentrated in vacuo. Chromatography of the yellow residual liquid down silica gel using 25:1 hexane:ethyl acetate gave 65 g (66%) of the title compound as oil.

Workup

  1. concentrationconcentrated in vacuo
  2. customThe organic layer was separated
  3. extractionthe aqueous layer is extracted with ethyl acetate (3×250 mL)
  4. washwashed with a saturated aqueous solution of sodium chloride (2×)
  5. customdried
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-6ddf23345de94c56b7f8f08a43f0fe2d
Source dataset
uspto-grants-2007_03
Patent number
US07196090B2

Reaction notes

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