HCID 14574999, compound → HCID 14575000, compound

HRID 1723071Notes

Reaction equation

HRID 1723071 reaction equation
[Br:1][CH:2]([C:6]1[C:10]2[CH:11]=[C:12]([Cl:15])[CH:13]=[CH:14][C:9]=2[O:8][N:7]=1)C(O)=O>C1(C)C=CC=CC=1>[Cl:15][C:12]1[CH:13]=[CH:14][C:9]2[O:8][N:7]=[C:6]([CH2:2][Br:1])[C:10]=2[CH:11]=1

Participants

3

Reactant 1

HCID 14574999HCID 14574999, compound

Product 1

HCID 14575000HCID 14575000, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
96 °C

Procedure

A suspension of alpha-bromo-5-chloro-1,2-benzisoxazole-3-acetic acid (3.39 Kg, 11.7 moles) in toluene (12 L) is heated at 96° C. for 18 hours. The solution is cooled to room temperature and washed with water (2×4 L), saturated sodium bicarbonate solution (2×4 L) and water (2×4 L) before drying over anhydrous sodium sulfate (1 Kg) and filtering. The filtrate is evaporated in vacuo to afford the crude 5-chloro-3-bromomethyl-1,2-benzisoxazole, m.p. 83°-85° C.

Workup

  1. temperatureThe solution is cooled to room temperature
  2. washwashed with water (2×4 L), saturated sodium bicarbonate solution (2×4 L) and water (2×4 L)
  3. dry with materialbefore drying over anhydrous sodium sulfate (1 Kg)
  4. filtrationfiltering
  5. customThe filtrate is evaporated in vacuo

Sources & evidence

ORD record
ord-4d1ff7c1e1a745b194c3dc69b9e92c26
Source dataset
uspto-grants-1989_08
Patent number
US04859691

Reaction notes

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