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

HRID 1032328Notes

Reaction equation

HRID 1032328 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-95b70d12fc1848e985b9e964cfe75c47
Source dataset
uspto-grants-1990_09
Patent number
US04957931

Reaction notes

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