4-Fluoroaniline → HCID 59437294, compound

HRID 244462Notes

Reaction equation

HRID 244462 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5](F)=[C:4]([N+:9]([O-:11])=[O:10])[CH:3]=1.[F:12][C:13]1[CH:18]=[CH:17][C:16]([NH2:19])=[CH:15][CH:14]=1.C(N(CC)C(C)C)(C)C>C(#N)C>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([NH:19][C:16]2[CH:17]=[CH:18][C:13]([F:12])=[CH:14][CH:15]=2)=[C:4]([N+:9]([O-:11])=[O:10])[CH:3]=1

Participants

5

Reactant 3

HCID 97314-FluoroanilineHCID 81531DiisopropylethylamineHCID 27363284-Bromo-1-fluoro-2-nitrobenzene

Product 1

HCID 59437294HCID 59437294, compoundYield 100.7%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
90 °C

Procedure

To a room temperature solution of 4-bromo-1-fluoro-2-nitrobenzene (3.3 g, 15 mmol) and 4-fluorophenylamine (1.42 mL, 15 mmol) in anhydrous acetonitrile (20 mL) was added N,N-diisopropylethylamine (2.9 mL, 16.5 mmol) and the mixture was warmed to 90° C. After 24 hours, the mixture was concentrated in vacuo and the crude material was purified by column chromatography over silica gel eluting with 0-20% ethyl acetate in hexanes to afford 4.7 g of (4-bromo-2-nitrophenyl)-(4-fluorophenyl)amine as an orange oil which solidified on standing. MS m/z 311/313 (MH+).

Workup

  1. concentrationthe mixture was concentrated in vacuo
  2. customthe crude material was purified by column chromatography over silica gel eluting with 0-20% ethyl acetate in hexanes

Sources & evidence

ORD record
ord-34fb1c345fc94d118fb6a9c691c9cf91
Source dataset
uspto-grants-2014_02
Patent number
US08658637B2

Reaction notes

Loading…