Sodium Carbonate → HCID 22730862, compound

HRID 2085675Notes

Reaction equation

HRID 2085675 reaction equation
Br[C:2]1[S:3][C:4]([Cl:7])=[CH:5][CH:6]=1.OB(O)[C:10]1[CH:18]=[CH:17][C:13]([C:14]([OH:16])=[O:15])=[CH:12][CH:11]=1.C([O-])([O-])=O.[Na+].[Na+]>COCCOC.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>[Cl:7][C:4]1[S:3][CH:2]=[CH:6][C:5]=1[C:10]1[CH:18]=[CH:17][C:13]([C:14]([OH:16])=[O:15])=[CH:12][CH:11]=1

Participants

6

Reactant 3

HCID 10340Sodium CarbonateHCID 761332-Bromo-5-chlorothiopheneHCID 3121834-Carboxyphenylboronic Acid

Product 1

HCID 22730862HCID 22730862, compound

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 80711,2-DimethoxyethaneSolvent2×

Conditions

Temperature
75 °C

Procedure

Solid Pd(PPh3)4 (11.0 mg, 0.01 mmol) was treated with a room temperature solution of 2-bromo-5-chlorothiophene (143 mg, 0.72 mmol) in DME (4 mL), stirred for 5 minutes, treated with a solution of 4-(dihydroxyboryl)benzoic acid (100 mg, 0.60 mmol) in DME (2 mL), and stirred for 5 minutes. The mixture was treated with 2M Na2CO3 (1.5 mL, 3.0 mmol), heated to 75° C., stirred for 18 hours, cooled to room temperature, filtered, triturated with water (3 mL), and concentrated. The concentrate was treated with boiling water (4 mL), filtered through celite, cooled to room temperature, adjusted to pH<7 with HCl, and filtered to provide the desired product. MS (APCI(+)) m/e 239 (M+H)+.

Workup

  1. stirringstirred for 5 minutes
  2. stirringstirred for 18 hours
  3. temperaturecooled to room temperature
  4. filtrationfiltered
  5. customtriturated with water (3 mL)
  6. concentrationconcentrated
  7. additionThe concentrate was treated with boiling water (4 mL)
  8. filtrationfiltered through celite
  9. temperaturecooled to room temperature
  10. filtrationfiltered

Sources & evidence

ORD record
ord-4b87262ca0e04aa7b560cc3270fea952
Source dataset
uspto-grants-2004_04
Patent number
US06720338B2

Reaction notes

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