2-Fluoroaniline → HCID 19023587, compound

HRID 1590236Notes

Reaction equation

HRID 1590236 reaction equation
[F:1][C:2]1[CH:8]=[CH:7][CH:6]=[CH:5][C:3]=1[NH2:4].[C:9]([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])(=[O:12])[CH:10]=[CH2:11].[Sn](Cl)(Cl)(Cl)Cl>C1C=CC=CC=1>[F:1][C:2]1[CH:8]=[CH:7][CH:6]=[CH:5][C:3]=1[NH:4][CH2:11][CH2:10][C:9]([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12]

Participants

5

Reactant 3

HCID 95842-FluoroanilineHCID 15458tert-Butyl acrylateHCID 24287Tin tetrachloride

Product 1

HCID 19023587HCID 19023587, compoundYield 11.4%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

To a solution of 2-fluoroaniline (22.06 g, 0.198 mol) and freshly distilled tert-butyl acrylate (25.145 g, 0.198 mol) in dry benzene (250 ml) was added tin tetrachloride (1 ml) and the mixture was refluxed for 60 h. The resulting suspension was filtered and the filtrate was evaporated to give a semisolid which was chromatographed on silica gel eluting with 25/75 ethyl acetate/hexane to give the title compound (5.4 g, 11%). Anal calcd for C13H18NO2F: C, 65.25; H, 7.58; N, 5.85. Found: C, 65.49; H, 7.75; N, 5.80. MS M+1 calcd for C13H18NO2F 240, found 240.

Workup

  1. temperaturethe mixture was refluxed for 60 h
  2. filtrationThe resulting suspension was filtered
  3. customthe filtrate was evaporated
  4. customto give a semisolid which
  5. customwas chromatographed on silica gel eluting with 25/75 ethyl acetate/hexane

Sources & evidence

ORD record
ord-24077d70eee14ad9ac6857ee158e8841
Source dataset
uspto-grants-1993_04
Patent number
US05202344

Reaction notes

Loading…