Boron tribromide → HCID 136133842, compound

HRID 929751Notes

Reaction equation

HRID 929751 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[O:10][N:9]=[C:8]([C:11]2[CH:16]=[CH:15][C:14]([O:17]C)=[CH:13][CH:12]=2)[CH:7]=1)=[O:5])[CH3:2].B(Br)(Br)Br>C(Cl)Cl>[CH2:1]([O:3][C:4]([C:6]1[O:10][N:9]=[C:8]([C:11]2[CH:12]=[CH:13][C:14]([OH:17])=[CH:15][CH:16]=2)[CH:7]=1)=[O:5])[CH3:2]

Participants

4

Reactant 2

HCID 25134Boron tribromideHCID 776513Ethyl 3-(4-methoxyphenyl)isoxazole-5-carboxylate

Product 1

HCID 136133842HCID 136133842, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

3-(4-Methoxy-phenyl)-isoxazole-5-carboxylic acid ethyl ester (available from ChemDiv Inc., 6605 Nancy Ridge Dr, San Diego, Calif., 92121, USA; 15 g, 60.1 mmol) was taken up in CH2Cl2 (30 mL) and 1 M BBr3 (400 mL, 400 mmol) was added. The reaction mixture was stirred at room temperature overnight. The mixture was added to a beaker of ice-water and the solid was collected by filtration. The solid was taken up in EtOAc and the solution was washed with water to remove most of the undesired carboxylic acid side product. Yield: 1.9 g (14%).

Workup

  1. filtrationthe solid was collected by filtration
  2. washthe solution was washed with water
  3. customto remove most of the undesired carboxylic acid side product

Sources & evidence

ORD record
ord-5962de56e9d749b490a59f486be2b86d
Source dataset
uspto-grants-2016_03
Patent number
US09296711B2

Reaction notes

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