4-Fluoroaniline → Tert-butyl (4-{[(4-fluorophenyl)imino]methyl}phenoxy)acetate

HRID 254109Notes

Reaction equation

HRID 254109 reaction equation
[CH:1]([C:3]1[CH:17]=[CH:16][C:6]([O:7][CH2:8][C:9]([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:10])=[CH:5][CH:4]=1)=O.[F:18][C:19]1[CH:25]=[CH:24][C:22]([NH2:23])=[CH:21][CH:20]=1>C1(C)C=CC=CC=1>[F:18][C:19]1[CH:25]=[CH:24][C:22]([N:23]=[CH:1][C:3]2[CH:17]=[CH:16][C:6]([O:7][CH2:8][C:9]([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:10])=[CH:5][CH:4]=2)=[CH:21][CH:20]=1

Participants

4

Reactant 2

HCID 97314-FluoroanilineHCID 639902Tert-butyl 2-(4-formylphenoxy)acetate

Product 1

HCID 86619087Tert-butyl (4-{[(4-fluorophenyl)imino]methyl}phenoxy)acetateYield 101.2%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

tert-Butyl (4-formylphenoxy)acetate (21.6 g, 0.09 mol) was dissolved in dry toluene (150 ml) and 4-fluoroaniline (8.8 ml, 0.091 mol) was added. The mixture was refluxed in a Dean-Stark apparatus for 23 hours, cooled and concentrated under reduced pressure. Addition of hexane and concentration under reduced pressure afforded 30.0 g (quant. yield) of the title compound as an off-white solid. NMR (200 MHz): 1.5 (s, 9H), 4.6 (s, 2H), 7.0-7.2 (m, 6H), 7.8 (d, 2H), 8.4 (s, 1H).

Workup

  1. temperatureThe mixture was refluxed in a Dean-Stark apparatus for 23 hours
  2. temperaturecooled
  3. concentrationconcentrated under reduced pressure
  4. additionAddition of hexane and concentration under reduced pressure

Sources & evidence

ORD record
ord-c4ca602c1d0e40c5afa31d8d11420762
Source dataset
uspto-grants-2011_01
Patent number
US07871998B2

Reaction notes

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