2-Fluoroaniline → HCID 19023587, compound

HRID 1034215Notes

Reaction equation

HRID 1034215 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 (25.45 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.

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-db444a49927241388eeb8f9d724e38ba
Source dataset
uspto-grants-1994_05
Patent number
US05314886

Reaction notes

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