Hydroxyamine hydrochloride → 6-Bromo-3-methyl-1,2-benzoxazole

HRID 2070878Notes

Reaction equation

HRID 2070878 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5](/[C:8](=[N:10]/O)/[CH3:9])=[C:4]([OH:12])[CH:3]=1.BrC1C=CC(C(=O)C)=C(O)C=1.C([O-])(=O)C.[Na+].Cl.NO>O>[Br:1][C:2]1[CH:7]=[CH:6][C:5]2[C:8]([CH3:9])=[N:10][O:12][C:4]=2[CH:3]=1

Participants

6

Reactant 4

HCID 443297Hydroxyamine hydrochlorideHCID 517045Sodium AcetateHCID 107274031-(4-Bromo-2-hydroxyphenyl)ethan-1-oneHCID 136326591HCID 136326591, compound

Product 1

HCID 124113226-Bromo-3-methyl-1,2-benzoxazoleYield 63.4%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

(E)-1-(4-Bromo-2-hydroxyphenyl)ethanone oxime. To a solution of 1-(4-bromo-2-hydroxyphenyl)ethanone (2.8 g, 13.02 mmol) and water (10 mL) was added sodium acetate (1.602 g, 19.53 mmol) and hydroxylamine hydrochloride (1.176 g, 16.93 mmol). The mixture was allowed to stir at ambient temperature for 16 h. The solution was condensed under reduced pressure and diluted with water and sonicated. The resultant solid was filtered and dried under vacuum oven conditions to afford the title compound (1.90 g, 8.26 mmol, 63.4% yield). MS (ESI) m/z 230.3 [M]+, 232.4 [M+2]+.

Workup

  1. customcondensed under reduced pressure
  2. customsonicated
  3. filtrationThe resultant solid was filtered
  4. customdried under vacuum oven conditions

Sources & evidence

ORD record
ord-c8e14aa0ea3441628c8d7ed83df4f661
Source dataset
uspto-grants-2012_10
Patent number
US08299056B2

Reaction notes

Loading…