Chlorosuccinimide → 2-Chloro-4-(trifluoromethoxy)aniline

HRID 1824722Notes

Reaction equation

HRID 1824722 reaction equation
[F:1][C:2]([F:12])([F:11])[O:3][C:4]1[CH:10]=[CH:9][C:7]([NH2:8])=[CH:6][CH:5]=1.[Cl:13]N1C(=O)CCC1=O>C(#N)C>[Cl:13][C:9]1[CH:10]=[C:4]([O:3][C:2]([F:11])([F:12])[F:1])[CH:5]=[CH:6][C:7]=1[NH2:8]

Participants

4

Reactant 2

HCID 31398ChlorosuccinimideHCID 6008484-(Trifluoromethoxy)aniline

Product 1

HCID 27340842-Chloro-4-(trifluoromethoxy)aniline

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

Part A. A solution of 4-trifluoromethoxyaniline (12.0 mL, 88.8 mmol) and N-chlorosuccinimide (13.04 g, 97.7 mmol) in acetonitrile (90 mL) was heated to reflux for 12 h. After cooling, the solution was filtered and evaporated, and the residual material was separated by column chromatography (silica gel, 10:90 ethyl acetate-hexane) to afford the product, 2-chloro-4-trifluoromethoxyaniline, as a liquid. The product was further purified by distillation to afford 18.14 g (85.7 mmol, 97%) pure product, b.p. 50-60° C./5 mm Hg (bulb-to-bulb). 1H NMR (300 MHz, CDCl3): Δ 7.16 (1H, d, J=2.5 Hz), 6.96 (1H, dd, J=8.8, 2.5 Hz), 6.73 (1H, d, J=8.8 Hz), 4.08 (2H, br s). MS (H2O-GC/MS): m/e 214 (27), 213 (17), 212 (100).

Workup

  1. temperatureto reflux for 12 h
  2. temperatureAfter cooling
  3. filtrationthe solution was filtered
  4. customevaporated
  5. customthe residual material was separated by column chromatography (silica gel, 10:90 ethyl acetate-hexane)

Sources & evidence

ORD record
ord-eb35199aada245fab8a6e326ddb61a53
Source dataset
uspto-grants-2006_05
Patent number
US07045529B2

Reaction notes

Loading…