Bromobenzene → 3-Phenyl-2-thiophenecarboxaldehyde

HRID 1169622Notes

Reaction equation

HRID 1169622 reaction equation
[CH:1]([C:3]1[S:4][CH:5]=[CH:6][C:7]=1B(O)O)=[O:2].Br[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.C([O-])([O-])=O.[Na+].[Na+]>C(O)C.C1C=CC=CC=1.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:12]1([C:7]2[CH:6]=[CH:5][S:4][C:3]=2[CH:1]=[O:2])[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1

Participants

7

Reactant 3

HCID 7961BromobenzeneHCID 10340Sodium CarbonateHCID 27734262-Formyl-3-thiopheneboronic acid

Product 1

HCID 8188473-Phenyl-2-thiophenecarboxaldehydeYield 53.6%

Reagents, catalysts & solvents 3

HCID 178418397HCID 178418397, compoundCatalystHCID 241BenzeneSolventHCID 702EthanolSolvent

Procedure

2-Formylthiophen-3-boronic acid (4) (0.89 g, 5.7 mmol) dissolved in 96% ethanol (15 ml) was added dropwise to a mixture of 2-bromobenzene (0.66 ml, 6.2 mmol) in benzene (12 ml), (Ph3P)4Pd (197 mg, 0.15 mmol) and an aqueous solution of 2M Na2CO3 (6.3 ml). The reaction mixture was then refluxed for 6 hrs. Then the mixture was cooled to room temperature, the solvent was partially removed under reduced pressure and the resulting mixture was extracted with ethyl ether (4×100 ml). The combined organic layer was washed with a saturated solution of NaCl, dried (Na2SO4), and evaporated under reduced pressure. The mixture was chromatographed using 95/5 petroleum ether/ethyl acetate, thus giving the derivative (5) (0.575 g, [lacuna] mmol, 53% yield).

Workup

  1. temperatureThe reaction mixture was then refluxed for 6 hrs
  2. customthe solvent was partially removed under reduced pressure
  3. extractionthe resulting mixture was extracted with ethyl ether (4×100 ml)
  4. washThe combined organic layer was washed with a saturated solution of NaCl
  5. dry with materialdried (Na2SO4)
  6. customevaporated under reduced pressure
  7. customThe mixture was chromatographed

Sources & evidence

ORD record
ord-7e38c1d67dec427c9dcb908e0731b584
Source dataset
uspto-grants-2010_11
Patent number
US07825129B2

Reaction notes

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