Sodium Carbonate → 4'-Chloro-2fluoro-biphenyl-4-carbaldehyde

HRID 1778582Notes

Reaction equation

HRID 1778582 reaction equation
[F:1][C:2]1[CH:7]=[C:6]([CH:8]=[O:9])[CH:5]=[CH:4][C:3]=1B(O)O.[Cl:13][C:14]1[CH:19]=[CH:18][C:17](I)=[CH:16][CH:15]=1.C(=O)([O-])[O-].[Na+].[Na+]>Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.O.O1CCOCC1>[Cl:13][C:14]1[CH:19]=[CH:18][C:17]([C:3]2[CH:4]=[CH:5][C:6]([CH:8]=[O:9])=[CH:7][C:2]=2[F:1])=[CH:16][CH:15]=1

Participants

7

Reactant 3

HCID 10340Sodium CarbonateHCID 125101-Chloro-4-iodobenzeneHCID 162180452-Fluoro-4-formylbenzeneboronic acid

Product 1

HCID 814474984'-Chloro-2fluoro-biphenyl-4-carbaldehydeYield 90%

Reagents, catalysts & solvents 3

HCID 178418476HCID 178418476, compoundCatalystHCID 962WaterSolvent2×HCID 312751,4-DioxaneSolvent

Procedure

2-Fluoro-4-formylphenyl boronic acid (263 mg, 1.57 mmol) was added to the mixture of 1-chloro-4-iodobenzene (250 mg, 1.05 mmol), PdCl2(PPh3)2 (36 mg, 0.5 mmol), and disodium carbonate (332 mg, 3.13 mmol) in a solution of water (1 mL) and dioxane (2 mL). The mixture was reacted at 130° C. for 22 min in a microwave reactor. After cooling, water was added, and the mixture was extracted with ethylacetate. The organic solvent was dried over Na2SO4, filtered, and concentrated. The residue was purified by column chromatography on silica gel, eluting with ethyl acetate in heptane to give the title compound (220 mg, 0.94 mmol, 90%) as a white solid. 1H NMR (D2O) δ 10.02 (s, 1H), 7.75 (d, J=7.8 Hz, 1H), 7.67 (d, J=10.4 Hz, 1H), 7.60 (t, J=7.5 Hz, 1H), 7.53 (d, J=8.3 Hz, 2H), 7.46 (d, J=8.3 Hz, 2H).

Workup

  1. customThe mixture was reacted at 130° C. for 22 min in a microwave reactor
  2. temperatureAfter cooling
  3. extractionthe mixture was extracted with ethylacetate
  4. dry with materialThe organic solvent was dried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe residue was purified by column chromatography on silica gel
  8. washeluting with ethyl acetate in heptane

Sources & evidence

ORD record
ord-8b4f89322c6c48f3b4a8db45d41c52bd
Source dataset
uspto-grants-2016_02
Patent number
US09266908B2

Reaction notes

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