Potassium Carbonate → 5-Phenylthiophene-2-carbaldehyde

HRID 1909798Notes

Reaction equation

HRID 1909798 reaction equation
Br[C:2]1[S:6][C:5]([CH:7]=[O:8])=[CH:4][CH:3]=1.[C:9]1(B(O)O)[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1.C([O-])([O-])=O.[K+].[K+]>C(O)(C)C.O.[Pd]>[C:9]1([C:2]2[S:6][C:5]([CH:7]=[O:8])=[CH:4][CH:3]=2)[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 66827Phenylboronic AcidHCID 784285-Bromothiophene-2-carbaldehyde

Product 1

HCID 1770535-Phenylthiophene-2-carbaldehydeYield 96.1%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 21889133Propan-2-ol--water (1/1)Solvent

Procedure

A mixture of 5-bromo-thiophene-2-carbaldehyde (2.0 g, 10.5 mmol), phenylboronic acid (1.7 g, 11 mmol), K2CO3 (8.7 g, 62.8 mmol) and 10% Pd/C (0.56 g) in isopropanol/H2O (1:1, 40 mL) was refluxed for 5 h. The reaction mixture was filtered through a pad of Celite. After the isopropanol was removed, the product was collected on a filter, washed with hexane and dried in vacuo to yield the title compound (1.9 g, 82%).

Workup

  1. temperaturewas refluxed for 5 h
  2. filtrationThe reaction mixture was filtered through a pad of Celite
  3. customAfter the isopropanol was removed
  4. customthe product was collected on a filter
  5. washwashed with hexane
  6. customdried in vacuo

Sources & evidence

ORD record
ord-ff215b38efb242c4937a45c4f5e15d62
Source dataset
uspto-grants-2013_12
Patent number
US08598359B2

Reaction notes

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