Water → HCID 135500024, compound

HRID 1061852Notes

Reaction equation

HRID 1061852 reaction equation
[Br:1]Br.[OH:3][C:4]1[CH:5]=[C:6]2[C:11](=[CH:12][CH:13]=1)[CH:10]=[C:9]([C:14]1[C:18]3[CH:19]=[CH:20][C:21]([OH:23])=[CH:22][C:17]=3[O:16][N:15]=1)[CH:8]=[CH:7]2.O>C(O)(=O)C>[Br:1][C:5]1[C:4]([OH:3])=[CH:13][CH:12]=[C:11]2[C:6]=1[CH:7]=[CH:8][C:9]([C:14]1[C:18]3[CH:19]=[CH:20][C:21]([OH:23])=[CH:22][C:17]=3[O:16][N:15]=1)=[CH:10]2

Participants

5

Reactant 3

HCID 962WaterHCID 24408BromineHCID 5287551HCID 5287551, compound

Product 1

HCID 135500024HCID 135500024, compoundYield 53%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent2×

Procedure

Bromine (0.11 mL, 2.17 mmol) in acetic acid (3 mL) was added dropwise into cold (5° C.) mixture of 3-(6-hydroxy-2-naphthyl)-1,2-benzisoxazol-6-ol (0.6 g, 2.17 mmol) and acetic acid (10 mL). The mixture was stirred for 30 min, poured into water and extracted with EtOAc. The organic extracts were dried over MgSO4. Evaporation and purification by flash chromatography (hexanes/EtOAc 1/1) gave an off-white solid (0.41 g, 53% yield, m.p. 275-277° C.); MS m/e 354 (M−H)+.

Workup

  1. extractionextracted with EtOAc
  2. dry with materialThe organic extracts were dried over MgSO4
  3. customEvaporation and purification by flash chromatography (hexanes/EtOAc 1/1)

Sources & evidence

ORD record
ord-b4c3819d64ee45559bf7daa212aaa85e
Source dataset
uspto-grants-2005_11
Patent number
US06960607B2

Reaction notes

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