Phenylboronic Acid → HCID 23033929, compound

HRID 1393352Notes

Reaction equation

HRID 1393352 reaction equation
C(=O)(O)[O-].[Na+].Br[C:7]1[S:8][C:9]2[C:15]([C:16]([OH:18])=[O:17])=[CH:14][CH:13]=[CH:12][C:10]=2[N:11]=1.[C:19]1(B(O)O)[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1>O.C(COC)OC.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.[Cu]I>[C:19]1([C:7]2[S:8][C:9]3[C:15]([C:16]([OH:18])=[O:17])=[CH:14][CH:13]=[CH:12][C:10]=3[N:11]=2)[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1

Participants

8

Reactant 3

HCID 66827Phenylboronic AcidHCID 516892Sodium BicarbonateHCID 230338792-Bromo-1,3-benzothiazole-7-carboxylic acid

Product 1

HCID 23033929HCID 23033929, compoundYield 78.3%

Reagents, catalysts & solvents 4

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 178418397HCID 178418397, compoundCatalystHCID 962WaterSolventHCID 80711,2-DimethoxyethaneSolvent

Conditions

Temperature
50 °C

Procedure

Tetrakis(triphenylphosphine)palladium (144 mg, 0.125 mmol) and a solution of sodium bicarbonate (630 mg, 7.50 mmol) in degassed water (10 ml) were added in turn to a solution of ethyl ester of 2-bromobenzothiazole-7-carboxylic acid (715 mg, 2.50 mmol) and phenyl boronic acid (341 mg, 2.8 mmol) in degassed dimethoxyethane (20 ml) and the mixture was stirred at 50° C. for 10 min. Copper (I) iodide (24 mg, 0.125 mmol) was added to the mixture at room temperature and the mixture was heated under reflux for 4 hrs. Dimethoxyethane was distilled off under reduced pressure and the residue was extracted with ethyl acetate. The organic layer was washed with brine and dried and the solvent was distilled off under reduced pressure. The residue was purified by column chromatography on silica gel (n-hexane/ethyl acetate=10) to give ethyl ester of 2-phenylbenzothiazole-7-carboxylic acid (500 mg, 70%) as colorless crystals.

Workup

  1. temperaturethe mixture was heated
  2. temperatureunder reflux for 4 hrs
  3. distillationDimethoxyethane was distilled off under reduced pressure
  4. extractionthe residue was extracted with ethyl acetate
  5. washThe organic layer was washed with brine
  6. customdried
  7. distillationthe solvent was distilled off under reduced pressure
  8. customThe residue was purified by column chromatography on silica gel (n-hexane/ethyl acetate=10)

Sources & evidence

ORD record
ord-74687d80904c4c35b0ab8edea982053f
Source dataset
uspto-grants-2008_03
Patent number
US07345068B2

Reaction notes

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