Toluene → 3-(Furan-3-yl)benzaldehyde

HRID 1840142Notes

Reaction equation

HRID 1840142 reaction equation
C1(C)C=CC=CC=1.Br[C:9]1[CH:13]=[CH:12][O:11][CH:10]=1.[CH:14]([C:16]1[CH:17]=[C:18](B(O)O)[CH:19]=[CH:20][CH:21]=1)=[O:15].C([O-])([O-])=O.[K+].[K+]>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.O.CN(C=O)C>[O:11]1[CH:12]=[CH:13][C:9]([C:20]2[CH:21]=[C:16]([CH:17]=[CH:18][CH:19]=2)[CH:14]=[O:15])=[CH:10]1

Participants

8

Reactant 4

HCID 1140TolueneHCID 11430Potassium CarbonateHCID 891643-BromofuranHCID 27343563-Formylphenylboronic acid

Product 1

HCID 235060103-(Furan-3-yl)benzaldehydeYield 10%

Reagents, catalysts & solvents 3

HCID 178418397HCID 178418397, compoundCatalystHCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

EX-601A) To a toluene (10 mL) solution of 3-bromofuran (0.54 mL, 6.0 mmol) was added 3-formylphenylboronic acid (1.00 g, 6.7 mmol) and DMF (4 mL). To the resulting solution was added K2CO3 (1.85 g, 13.4 mmol) and Pd(PPh3)4 (0.40 g, 0.35 mmol). The slurry was heated to reflux under argon for 2 h. The cooled mixture was poured into water and extracted with ethyl acetate. The organic layer was washed with brine, dried (MgSO4) and evaporated to an oil. Purification by flash chromatography on silica gel eluting with 5% ethyl acetate in hexane gave 0.10 g (10%) of the desired 3-(3-furanyl)benzaldehyde product as a yellow oil. MS: m/z=173.0 [M+H]+.

Workup

  1. temperatureThe slurry was heated
  2. temperatureto reflux under argon for 2 h
  3. extractionextracted with ethyl acetate
  4. washThe organic layer was washed with brine
  5. dry with materialdried (MgSO4)
  6. customevaporated to an oil
  7. customPurification by flash chromatography on silica gel eluting with 5% ethyl acetate in hexane

Sources & evidence

ORD record
ord-7b9e5aa8afaf45cf949ceb347d1741dd
Source dataset
uspto-grants-2004_01
Patent number
US06677380B2

Reaction notes

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