Diethyl Ether → 5-Phenylthiophene-2-carbaldehyde

HRID 896459Notes

Reaction equation

HRID 896459 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.[Na+].[Na+].CCOCC>C1COCC1.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>[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

7

Reactant 4

HCID 3283Diethyl EtherHCID 10340Sodium CarbonateHCID 66827Phenylboronic AcidHCID 784285-Bromothiophene-2-carbaldehyde

Product 1

HCID 1770535-Phenylthiophene-2-carbaldehydeYield 91.9%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 8028TetrahydrofuranSolvent2×

Procedure

5-Bromothiophene-2-carboxaldehyde (1.0 g, 5.2 mmol) is added to a solution of tetrakis(triphenylphosphine)palladium(0) (180 mg, 0.16 mmol) in degassed THF (10 mL). The resulting solution is stirred for 5 min. A solution of phenylboronic acid (760 mg, 6.2 mmol) in THF (10 mL) is added followed by aqueous Na2CO3 (2M, 5.2 mL). The mixture is heated at reflux for 24 h. The reaction mixture is allowed to cool, poured into ether, and washed twice with water. The ether layer is dried over Na2SO4 and concentrated in vacuo. The crude product is purified by flash column chromatography (1:1 hexanes:CH2Cl2) to yield 5-phenylthiophene-2-carboxaldehyde (900 mg, 91%). 1H NMR (300 MHz, CDCl3) δ 7.38-7.45, 7.65-7.68, 7.73, 9.88.

Workup

  1. temperatureThe mixture is heated
  2. temperatureat reflux for 24 h
  3. temperatureto cool
  4. washwashed twice with water
  5. dry with materialThe ether layer is dried over Na2SO4
  6. concentrationconcentrated in vacuo
  7. customThe crude product is purified by flash column chromatography (1:1 hexanes:CH2Cl2)

Sources & evidence

ORD record
ord-b219a1c2ce2244b2b84628d4faca98d4
Source dataset
uspto-grants-2005_07
Patent number
US06919359B2

Reaction notes

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