Benzene → 5-(2-Methoxyphenyl)-2-furancarboxaldehyde

HRID 2281027Notes

Reaction equation

HRID 2281027 reaction equation
C1C=CC=CC=1.Br[C:8]1[O:12][C:11]([CH:13]=[O:14])=[CH:10][CH:9]=1.[CH3:15][O:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=1B(O)O.C([O-])([O-])=O.[K+].[K+]>C(OCC)(=O)C.[Pd].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>[CH3:15][O:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=1[C:8]1[O:12][C:11]([CH:13]=[O:14])=[CH:10][CH:9]=1

Participants

7

Reactant 4

HCID 241BenzeneHCID 11430Potassium CarbonateHCID 6003285-Bromofuran-2-carbaldehydeHCID 27339582-Methoxyphenylboronic acid

Product 1

HCID 46749915-(2-Methoxyphenyl)-2-furancarboxaldehydeYield 65%

Reagents, catalysts & solvents 2

HCID 11979704Tetrakis(triphenylphosphine)palladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

To a benzene (10 mL) solution of 5-bromo-2-furaldehyde 7 (350 mg, 2.0 mmol) and 2-methoxyphenylboronic acid 8 (304 mg, 2.0 mmol) was added tetrakis(triphenylphosphine)-palladium(0) (69.4 mg, 0.06 mmol) and sat. aq. K2CO3 solution (4.94 ml, 4.0 mmol) at 21° C. under an argon atmosphere. The reaction mixture was refluxed for 2 h. The mixture was then cooled and diluted with ethyl acetate (100 mL). The organic layer was washed with water (2×20 mL), then dried with brine and MgSO4 and concentrated in vacuo. Flash column chromatography on silica gel (hexane:ethyl acetate=20:1) of the residue afforded 5-(2-methoxyphenyl)-2-furaldehyde 9 in 65% yield (265 mg, yellow oil). 1H NMR (400 MHz, CDCl3): δ 9.65 (s, 1H), 8.05 (dd, J=8.0, 2.0 Hz, 1H), 7.39-7.35 (m, 1H), 7.33 (d, J=3.6 Hz, 1H), 7.14 (d, J=4.0 Hz, 1H), 7.07 (dt, J=7.2, 0.8 Hz, 1H), 7.00 (bd, J=8.0 Hz, 1H), 3.97 (s, 3H).

Workup

  1. temperatureThe reaction mixture was refluxed for 2 h
  2. temperatureThe mixture was then cooled
  3. washThe organic layer was washed with water (2×20 mL)
  4. dry with materialdried with brine and MgSO4
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-0e892f5884024ecdb4c10607e10804a3
Source dataset
uspto-grants-2015_09
Patent number
US09139575B2

Reaction notes

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