Hydrochloric Acid → HCID 21833736, compound

HRID 2392632Notes

Reaction equation

HRID 2392632 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([C:8]2[O:12][N:11]=[C:10]([CH3:13])[N:9]=2)=[CH:4][C:3]=1[CH3:14].B([C:18]1[CH:26]=[CH:25][C:21]([C:22]([OH:24])=[O:23])=[CH:20][CH:19]=1)(O)O.C(=O)([O-])[O-].[Na+].[Na+].Cl>COCCOC.O.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[CH3:14][C:3]1[CH:4]=[C:5]([C:8]2[O:12][N:11]=[C:10]([CH3:13])[N:9]=2)[CH:6]=[CH:7][C:2]=1[C:18]1[CH:26]=[CH:25][C:21]([C:22]([OH:24])=[O:23])=[CH:20][CH:19]=1

Participants

8

Reactant 4

HCID 313Hydrochloric AcidHCID 10340Sodium CarbonateHCID 3121834-Carboxyphenylboronic AcidHCID 218337875-(4-Bromo-3-methylphenyl)-3-methyl-1,2,4-oxadiazole

Product 1

HCID 21833736HCID 21833736, compoundYield 80%

Reagents, catalysts & solvents 3

HCID 178418397HCID 178418397, compoundCatalystHCID 962WaterSolventHCID 80711,2-DimethoxyethaneSolvent

Procedure

A stirred solution of 5-(4-bromo-3-methylphenyl)-3-methyl-1,2,4-oxadiazole (EP 0533268 A1) (0.65 g, 0.0026 mole) in a mixture of DME (30 ml) and water (30 ml) under argon was treated with 4-boronobenzoic acid (0.43 g, 0.0026 mole), sodium carbonate (1.16 g, 0.011 mole) and tetrakis(triphenylphosphine)palladium(0) (40 mg), then heated under reflux for 4 hours. The mixture was acidified with 1M hydrochloric acid and extracted with ethyl acetate. The extract was dried (Na2SO4) and concentrated in vacuo to leave the title compound as a white solid (0.61 g, 80%).

Workup

  1. temperatureheated
  2. temperatureunder reflux for 4 hours
  3. extractionextracted with ethyl acetate
  4. dry with materialThe extract was dried (Na2SO4)
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-0cbe4979c6db46fdb7ae5f4fa5641849
Source dataset
uspto-grants-1998_09
Patent number
US05801170

Reaction notes

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