Water → HCID 21704933, compound

HRID 1595264Notes

Reaction equation

HRID 1595264 reaction equation
O[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[CH:9]=[CH:10][C:11]2[C:12]([CH:16]=1)=[N:13][O:14][N:15]=2.[Br-:17].[Br-].[Br-].C([N+](CCCC)(CCCC)CCCC)CCC.C([N+](CCCC)(CCCC)CCCC)CCC.C([N+](CCCC)(CCCC)CCCC)CCC.[OH2:71]>ClCCl>[Br:17][C:7]1[CH:2]=[C:3]([C:8]2[CH:9]=[CH:10][C:11]3[C:12]([CH:16]=2)=[N:13][O:14][N:15]=3)[CH:4]=[C:5]([OH:71])[CH:6]=1

Participants

5

Reactant 3

HCID 962WaterHCID 23500184Tetra-n-butylammonium tribromideHCID 135592938HCID 135592938, compound

Product 1

HCID 21704933HCID 21704933, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
18 °C

Procedure

A stirred mixture of 5-(2-hydroxyphenyl)benzofurazan (11.2 g, 52.8 mmol), and tetrabutylammonium tribromide (25.5 g, 52.8 mmol) in dichoromethane (530 mL) is stirred at 18° C. for 18 h. The solvent is evaporated off under reduced pressure to yield a residue which is treated with water (300 mL) and extracted with ethyl acetate (3×100 mL). The combined extracts are washed (saturated NaCl), dried (Na2SO4), filtered and the solvent is evaporated off under reduced pressure to yield the crude product which is purified by recrystallisation from ethyl acetate-hexane to give 5-(3-bromo-5-hydroxyphenyl)benzofurazan as a pale-yellow crystalline solid, m.p. 179-181° C.

Workup

  1. customThe solvent is evaporated off under reduced pressure
  2. customto yield a residue which
  3. extractionextracted with ethyl acetate (3×100 mL)
  4. washThe combined extracts are washed (saturated NaCl)
  5. dry with materialdried (Na2SO4)
  6. filtrationfiltered
  7. customthe solvent is evaporated off under reduced pressure
  8. customto yield the crude product which
  9. customis purified by recrystallisation from ethyl acetate-hexane

Sources & evidence

ORD record
ord-fe239059c4164c40b45b34f6431d2e25
Source dataset
uspto-grants-2001_09
Patent number
US06288092B1

Reaction notes

Loading…