Nitrogen → 7-Bromo-3-chloro-6-methoxy-1,2-benzisoxazole

HRID 2396725Notes

Reaction equation

HRID 2396725 reaction equation
[Cl:1][C:2]1[C:6]2[CH:7]=[CH:8][C:9]([O:11][CH3:12])=[CH:10][C:5]=2[O:4][N:3]=1.[Br:13]Br.N#N.CC(C)=O.C(Cl)(Cl)(Cl)Cl>C(O)(=O)C>[Br:13][C:10]1[C:5]2[O:4][N:3]=[C:2]([Cl:1])[C:6]=2[CH:7]=[CH:8][C:9]=1[O:11][CH3:12]

Participants

6

Reactant 4

HCID 947NitrogenHCID 24408Bromine2×HCID 158169243-Chloro-6-methoxy-1,2-benzoxazoleHCID 19595110CCl4 acetone

Product 1

HCID 187964507-Bromo-3-chloro-6-methoxy-1,2-benzisoxazole

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent3×

Procedure

To a stirred solution of 3-chloro-6-methoxy-1,2-benzisoxazole (25 g) in acetic acid (200 ml) was added a solution of bromine (32.6 g) in acetic acid (100 ml) dropwise under N2 at ambient temperature. The mixture was allowed to stir overnight. TLC (silica gel, 5% acetone/CCl4) revealed the presence of starting material. Additional bromine (11 g) in acetic acid (50 ml) was added, and the reaction mixture was allowed to stir overnight. The reaction was filtered and washed with water. The precipitate was collected and recrystallized from methanol to yield the desired compound, m.p. 134°-135° C.

Workup

  1. stirringto stir overnight
  2. filtrationThe reaction was filtered
  3. washwashed with water
  4. customThe precipitate was collected
  5. customrecrystallized from methanol

Sources & evidence

ORD record
ord-0172d78220634b63bd25f3290f1bb457
Source dataset
uspto-grants-1996_02
Patent number
US05494908

Reaction notes

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