Toluene → 3-(Furan-3-yl)benzaldehyde

HRID 990525

Reaction equation

HRID 990525 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

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-d331e814c22b41ca998605fc7d95bf70
Source dataset
uspto-grants-2002_10
Patent number
US06458852B1

Linked notes

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