Tetrahydrofuran → Butyl (2-fluorophenyl)carbamate

HRID 844996Notes

Reaction equation

HRID 844996 reaction equation
[F:1][C:2]1[CH:8]=[CH:7][CH:6]=[CH:5][C:3]=1[NH2:4].C(O[C:14](=[O:20])[O:15][C:16]([CH3:19])(C)C)(C)(C)C.[CH2:21]1COC[CH2:22]1>>[CH2:16]([O:15][C:14]([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-butylcarbonate (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 with 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-0cfd1302c4f1416db8aacad0580f557c
Source dataset
uspto-grants-1988_07
Patent number
US04755212

Reaction notes

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