Tetrahydrofuran → Butyl (2-fluorophenyl)carbamate

HRID 1031391Notes

Reaction equation

HRID 1031391 reaction equation
[F:1][C:2]1[CH:8]=[CH:7][CH:6]=[CH:5][C:3]=1[NH2:4].[C:9](=[O:20])([O:15][C:16]([CH3:19])(C)C)OC(C)(C)C.[CH2:21]1COC[CH2:22]1>>[CH2:16]([O:15][C:9]([NH:4][C:3]1[CH:5]=[CH:6][CH:7]=[CH:8][C:2]=1[F:1])=[O:20])[CH2:19][CH2:21][CH3:22]

Participants

4

Reactant 3

HCID 8028TetrahydrofuranHCID 95842-FluoroanilineHCID 10219638Carbonic acid, bis(1,1-dimethylethyl) ester

Product 1

HCID 1562695Butyl (2-fluorophenyl)carbamate

Procedure

A solution of 2-fluoroaniline (30.0 g, 0.27 mol) and di-t-butyl carbonate (66.5 g, 0.30 mol) in 100 ml of THF was heated at reflux for 4 hours. The solvent was removed by evaporation at reduced pressure, and the residue was partitioned between 1M aqueous citric acid and ethyl acetate. The organic phase was washed with saturated aqueous NaCl. The solvent was removed to afford the desired product, which was used without further purification. IR and 1H NMR spectra were in agreement with the assigned structure.

Workup

  1. temperatureat reflux for 4 hours
  2. customThe solvent was removed by evaporation at reduced pressure
  3. customthe residue was partitioned between 1M aqueous citric acid and ethyl acetate
  4. washThe organic phase was washed with saturated aqueous NaCl
  5. customThe solvent was removed

Sources & evidence

ORD record
ord-c48855e0597145a7968659932543f5d0
Source dataset
uspto-grants-1990_09
Patent number
US04954163

Reaction notes

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