Water → 2-[4-Bromo-3-(2-oxazolylmethyl)phenyl]oxazole

HRID 1457186Notes

Reaction equation

HRID 1457186 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[O:9][CH:10]=[CH:11][N:12]=2)=[CH:4][C:3]=1[CH2:13][C:14](Cl)=[O:15].[NH:17]1[CH:21]=[CH:20]N=N1.C([O-])([O-])=O.[K+].[K+].O>S1(CCCC1)(=O)=O>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[O:9][CH:10]=[CH:11][N:12]=2)=[CH:4][C:3]=1[CH2:13][C:14]1[O:15][CH:20]=[CH:21][N:17]=1

Participants

6

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 221035042-Bromo-5-(2-oxazolyl)benzeneacetyl chlorideHCID 178418936HCID 178418936, compound

Product 1

HCID 221036352-[4-Bromo-3-(2-oxazolylmethyl)phenyl]oxazole

Reagents, catalysts & solvents 1

HCID 31347SulfolaneSolvent

Conditions

Temperature
140 °C

Procedure

A mixture of the title compound of Step (C), 1H-1,2,3-triazole (144 mg, 2.1 mmol) and K2CO3 (1.3 g, 9.5 mmol) in 3.8 ml sulfolane was heated at 140° C. for 3 hrs. After cooling, 30 ml H2O was added and the mixture was extracted with 1:1 EtOAc/hexane. The combined organic extracts were washed with H2O and brine, dried and concentrated. The residue was chromatographed on silica gel using 3:1 hexane/EtOAc to afford the title compound of this step (256 mg, 44% for three steps).

Workup

  1. temperatureAfter cooling
  2. extractionthe mixture was extracted with 1:1 EtOAc/hexane
  3. washThe combined organic extracts were washed with H2O and brine
  4. customdried
  5. concentrationconcentrated
  6. customThe residue was chromatographed on silica gel using 3:1 hexane/EtOAc

Sources & evidence

ORD record
ord-5071b268d378473c832f0a7f3b5fb46a
Source dataset
uspto-grants-1998_12
Patent number
US05846990

Reaction notes

Loading…