Potassium Carbonate → HCID 135592938, compound

HRID 2187525Notes

Reaction equation

HRID 2187525 reaction equation
Br[C:2]1[CH:3]=[CH:4][C:5]2[C:6]([CH:10]=1)=[N:7][O:8][N:9]=2.[OH:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=1B(O)O.C1(C)C=CC=CC=1P(C1C=CC=CC=1C)C1C=CC=CC=1C.C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O.C([O-])(=O)C.[Pd+2].C([O-])(=O)C.O>[OH:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=1[C:2]1[CH:3]=[CH:4][C:5]2[C:6]([CH:10]=1)=[N:7][O:8][N:9]=2

Participants

8

Reactant 4

HCID 11430Potassium CarbonateHCID 80271Tri-o-tolylphosphineHCID 2773454(2-Hydroxyphenyl)boronic acidHCID 27762985-Bromo-2,1,3-benzoxadiazole

Product 1

HCID 135592938HCID 135592938, compound

Reagents, catalysts & solvents 3

HCID 167845palladium(II) acetateCatalystHCID 962WaterSolvent2×HCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

A stirred mixture of 5-bromobenzofurazan (11.94 g, 60 mmol), 2-hydroxyphenylboronic acid (9.10 g, 66 mmol), tri-o-tolylphosphine (1.82 g, 6 mmol), palladium (II) acetate (0.672 g, 3 mmol), potassium carbonate (12.4 g, 90 mmol), and water (90 mL) in dimethylformamide (180 mL) is heated at 80° C. under an argon atmosphere for 30 minutes. The mixture is then 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 chromatography (silica gel, 20%-100% ethyl acetate in cyclohexane) and recrystallised from ethyl acetate-hexane to give 5-(2-hydroxyphenyl)benzofurazan as a pale-yellow crystalline solid, m.p. 166-169° C.

Workup

  1. extractionextracted with ethyl acetate (3×100 mL)
  2. washThe combined extracts are washed (saturated NaCl)
  3. dry with materialdried (Na2SO4)
  4. filtrationfiltered
  5. customthe solvent is evaporated off under reduced pressure
  6. customto yield the crude product which
  7. customis purified by chromatography (silica gel, 20%-100% ethyl acetate in cyclohexane)
  8. customrecrystallised from ethyl acetate-hexane

Sources & evidence

ORD record
ord-8413a75ddef3454f8440221ae1c14838
Source dataset
uspto-grants-2002_06
Patent number
US06410547B1

Reaction notes

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