Water → SEA0400

HRID 1275689Notes

Reaction equation

HRID 1275689 reaction equation
[CH2:1]([O:3][C:4]1[CH:5]=[CH:6][C:7]([O:11][C:12]2[CH:17]=[CH:16][C:15]([OH:18])=[CH:14][CH:13]=2)=[C:8]([CH:10]=1)[NH2:9])[CH3:2].CC(C)([O-])C.[K+].[F:25][C:26]1[CH:33]=[CH:32][C:31]([F:34])=[CH:30][C:27]=1[CH2:28]Br.O>CN(C)C=O>[F:25][C:26]1[CH:33]=[CH:32][C:31]([F:34])=[CH:30][C:27]=1[CH2:28][O:18][C:15]1[CH:16]=[CH:17][C:12]([O:11][C:7]2[CH:6]=[CH:5][C:4]([O:3][CH2:1][CH3:2])=[CH:10][C:8]=2[NH2:9])=[CH:13][CH:14]=1

Participants

6

Reactant 4

HCID 962WaterHCID 5228302-(Bromomethyl)-1,4-difluorobenzeneHCID 22117692HCID 22117692, compoundHCID 23665647Potassium tert-butoxide

Product 1

HCID 644100SEA0400Yield 77%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 5-ethoxy-2-(4-hydroxyphenoxy)aniline (3.68 g, 15 mmol) in N,N-dimethylformamide (50 ml) were added potassium tert-butoxide (2.02 g, 18 mmol) and 2,5-difluorobenzyl bromide (3.11 g, 15 mmol), followed by stirring at room temperature overnight. The reaction solution was poured into water and extracted with ethyl acetate. The organic layer was washed with water and a saturated aqueous sodium chloride solution, and after drying, the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography [eluent; ethyl acetate-hexane (1:4)] to give the title compound (4.29 g).

Workup

  1. extractionextracted with ethyl acetate
  2. washThe organic layer was washed with water
  3. dry with materiala saturated aqueous sodium chloride solution, and after drying
  4. customthe solvent was evaporated under reduced pressure
  5. customThe residue was purified by silica gel column chromatography [eluent; ethyl acetate-hexane (1:4)]

Sources & evidence

ORD record
ord-f805f754538540abba67fac53e9f5eac
Source dataset
uspto-grants-2000_12
Patent number
US06162832

Reaction notes

Loading…