2-(Benzo[d]isoxazol-3-yl)-2-bromoacetic acid → 1,2-Benzisoxazole, 3-(bromomethyl)-

HRID 1723073Notes

Reaction equation

HRID 1723073 reaction equation
[Br:1][CH:2]([C:6]1[C:10]2[CH:11]=[CH:12][CH:13]=[CH:14][C:9]=2[O:8][N:7]=1)C(O)=O>C1(C)C=CC=CC=1>[Br:1][CH2:2][C:6]1[C:10]2[CH:11]=[CH:12][CH:13]=[CH:14][C:9]=2[O:8][N:7]=1

Participants

3

Reactant 1

HCID 129470982-(Benzo[d]isoxazol-3-yl)-2-bromoacetic acid

Product 1

HCID 34991891,2-Benzisoxazole, 3-(bromomethyl)-

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

Alpha-bromo-1,2-benzisoxazole-3-acetic acid (58.0 g, 0.23 mole) is suspended in toluene (350 mL) and the mixture is stirred at reflux for 18 hours. The solvent is evaporated and the residue is taken up in methylene chloride (250 mL). This solution is washed with saturated aqueous sodium bicarbonate (2×50 mL), water (50 mL) and dried over anhydrous magnesium sulfate. The solution is filtered and evaporated to afford 3-bromomethyl-1,2-benzisoxazole, m.p. 60°-62° C. The compound is purified by recrystallisation from ether-hexane, m.p. 64°-66° C.

Workup

  1. temperatureat reflux for 18 hours
  2. customThe solvent is evaporated
  3. washThis solution is washed with saturated aqueous sodium bicarbonate (2×50 mL), water (50 mL)
  4. dry with materialdried over anhydrous magnesium sulfate
  5. filtrationThe solution is filtered
  6. customevaporated

Sources & evidence

ORD record
ord-e7246447aa0641109e516aedbc8653a4
Source dataset
uspto-grants-1989_08
Patent number
US04859691

Reaction notes

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