Bromine → HCID 178422393, compound

HRID 1375186Notes

Reaction equation

HRID 1375186 reaction equation
[CH3:1][C:2]1[CH:11]=[CH:10][C:5]2[C:6]([OH:9])=[N:7][O:8][C:4]=2[CH:3]=1.[Br:12]Br>C(O)(=O)C>[Br:12][C:11]1[C:2]([CH3:1])=[CH:3][C:4]2[O:8][N:7]=[C:6]([OH:9])[C:5]=2[CH:10]=1

Participants

4

Reactant 2

HCID 24408BromineHCID 178422984HCID 178422984, compound

Product 1

HCID 178422393HCID 178422393, compoundYield 96%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
80 °C

Procedure

A 25 ml high-pressure tube equipped with a stir bar and a screw-on Teflon cap was charged with 6-methyl-benzo[d]isoxazol-3-ol (745 mg, 5.0 mmole, 1.0 eq) and glacial acetic acid (5.0 ml). Neat Br2 (774 μL, 15.0 mmoles, 3.0 eq) was added dropwise. After stirring at 80° C. for 20 hours, the reaction was allowed to cool slowly to room temperature. The resulting precipitate was collected by filtration and washed quickly with 3×1.0 ml of glacial acetic acid. Crystallization of this crude product (624 mg) from 50 ml of MeCN yielded 567 mg of the title compound (96% purity determined RP-HPLC). Additional crystallization from 70 ml of toluene provided 519 mg (46%) as a white solid (98.1% purity determined by HPLC). (1H DMSO-d6, 400 MHz) δ 12.45 (s, 1H), 7.94 (s, 1H), 7.61 (s, 1H), 2.45 (s, 3H); (13C CD3OD, 100 MHz) δ 165.96, 164.50, 142.34, 125.39, 119.73, 115.78, 112.67, 24.10.

Workup

  1. customA 25 ml high-pressure tube equipped with a stir bar
  2. temperatureto cool slowly to room temperature
  3. filtrationThe resulting precipitate was collected by filtration
  4. washwashed quickly with 3×1.0 ml of glacial acetic acid
  5. customCrystallization of this crude product (624 mg) from 50 ml of MeCN

Sources & evidence

ORD record
ord-5d0a88950b244b238e4ad753a53bf28f
Source dataset
uspto-grants-2007_01
Patent number
US07166725B2

Reaction notes

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