Sodium Carbonate → HCID 22723452, compound

HRID 1581793Notes

Reaction equation

HRID 1581793 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([F:8])=[CH:4][C:3]=1[OH:9].[S:10]1[CH:14]=[CH:13][CH:12]=[C:11]1B(O)O.C(=O)([O-])[O-].[Na+].[Na+]>O1CCOCC1.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>[S:10]1[CH:14]=[CH:13][CH:12]=[C:11]1[C:2]1[CH:7]=[CH:6][C:5]([F:8])=[CH:4][C:3]=1[OH:9]

Participants

6

Reactant 3

HCID 10340Sodium CarbonateHCID 27246002-Bromo-5-fluorophenolHCID 27339602-Thiopheneboronic acid

Product 1

HCID 22723452HCID 22723452, compoundYield 74%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 312751,4-DioxaneSolvent

Conditions

Temperature
100 °C

Procedure

2-Bromo-5-fluoro-phenol (0.87 ml, 7.9 mmol) and 2-thiopheneboronic acid (2.02 g, 15.8 mmol) are dissolved in 100 ml dioxane. The resultingsolution is flushed with argon before tetrakis(triphenylphosphine)palladium (456 mg, 0.395 mmol) and 2 ml of aqueous 2M sodium carbonate solution (20 mmol) are added. After flushing again with argon the mixture is refluxed for 15 hours at 100° C. The solution is allowed to cool to room temperature and the mixture is filtered. The filtrate is evaporated and the residue is taken up in dichloromethane and extracted with water. The organic layer is dried with sodium sulfate then concentrated. The residue is purified by chromatography (CH2Cl2/EtOH gradient 100:0 to 98:2) to yield 1.13 g of 2-(thien-2-yl)-5-fluorophenol (74%).

Workup

  1. additionare added
  2. customAfter flushing again with argon the mixture
  3. temperatureto cool to room temperature
  4. filtrationthe mixture is filtered
  5. customThe filtrate is evaporated
  6. extractionextracted with water
  7. dry with materialThe organic layer is dried with sodium sulfate
  8. concentrationthen concentrated
  9. customThe residue is purified by chromatography (CH2Cl2/EtOH gradient 100:0 to 98:2)

Sources & evidence

ORD record
ord-1f843c34f6d445eaa9df52827e0f5d8d
Source dataset
uspto-grants-2004_05
Patent number
US06730792B2

Reaction notes

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