Hydrochloric Acid → 6-Fluoro-1,3-benzoxazol-2(3H)-one

HRID 2253568Notes

Reaction equation

HRID 2253568 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([F:8])=[CH:4][C:3]=1[OH:9].Cl[C:11](Cl)([O:13]C(=O)OC(Cl)(Cl)Cl)Cl.C1(O)C=CC=CC=1.Cl>N1C=CC=CC=1.C(Cl)Cl>[F:8][C:5]1[CH:6]=[CH:7][C:2]2[NH:1][C:11](=[O:13])[O:9][C:3]=2[CH:4]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 996PhenolHCID 94429Triphosgene2×HCID 1857632-Amino-5-fluorophenol

Product 1

HCID 144573586-Fluoro-1,3-benzoxazol-2(3H)-one

Reagents, catalysts & solvents 2

HCID 1049PyridineSolventHCID 6344DichloromethaneSolvent

Conditions

Temperature
60 °C

Procedure

2-amino-5-fluorophenol [4.0 grams (g) (0.03 moles) (M)] was dissolved in 40.0 ml pyridine. The mixture was cooled with an ice bath while triphosgene [3.5 g (0.03 M)] was added. The mixture was heated to 60° C. for 3.0 hours. Thin layer chromatography showed that some of the starting phenol was still present. The mixture was then cooled; triphosgene [0.35 g 0.003 M)] was added and heated to reflux for 4.0 hours. The mixture was cooled, methylene chloride and 10% hydrogen chloride solution was added and stirred to room temperature.

Workup

  1. additionwas added
  2. temperatureThe mixture was then cooled
  3. temperatureheated
  4. temperatureto reflux for 4.0 hours
  5. temperatureThe mixture was cooled

Sources & evidence

ORD record
ord-21a3d60b9e0b43abb3fe15517c1fc172
Source dataset
uspto-grants-1993_08
Patent number
US05232899

Reaction notes

Loading…