Sodium Carbonate → 5-Hydroxy-biphenyl-3-carbaldehyde

HRID 30619

Reaction equation

HRID 30619 reaction equation
O[C:2]1[CH:3]=[C:4]([CH:7]=[C:8]([OH:10])[CH:9]=1)[CH:5]=[O:6].FC(F)(F)S(OS(C(F)(F)F)(=O)=O)(=O)=O.[C:26]1(B(O)O)[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1.C(=O)([O-])[O-].[Na+].[Na+]>C(Cl)Cl.COCCOC.O.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.N1C=CC=CC=1>[OH:10][C:8]1[CH:7]=[C:4]([CH:5]=[O:6])[CH:3]=[C:2]([C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)[CH:9]=1

Participants

10

Reactant 4

HCID 10340Sodium CarbonateHCID 66827Phenylboronic AcidHCID 67749Trifluoromethanesulfonic anhydrideHCID 943653,5-Dihydroxybenzaldehyde

Product 1

HCID 858888835-Hydroxy-biphenyl-3-carbaldehyde

Reagents, catalysts & solvents 5

HCID 178418476HCID 178418476, compoundCatalystHCID 962WaterSolventHCID 1049PyridineSolvent2×HCID 6344DichloromethaneSolventHCID 80711,2-DimethoxyethaneSolvent

Procedure

A solution of 3,5-dihydroxybenzaldehyde (14.4 mmol) and pyridine (114 mmol) in methylene chloride (20 ml) was slowly added trifluoromethanesulfonic anhydride (36.2 mmol) keeping the temperature below 5° C. After 10 min the mixture was washed with water and the organic phase was concentrated under reduced pressure. The crude brown crystals (6.4 g—product and pyridine −1:1), phenylboronic acid (13.2 mmol), sodium carbonate (39.6 mmol) and dichlorobis(triphenylphosphine)-palladium (II). (3 mol %) was dissolved in DME (40 ml) and water (20 ml). The mixture was refluxed for 17 h under Argon, cooled to room temperature and extracted with ethyl acetate. Purification by chromatography yielded 5-Hydroxy-biphenyl-3-carbaldehyde

Workup

  1. customthe temperature below 5° C
  2. washAfter 10 min the mixture was washed with water
  3. concentrationthe organic phase was concentrated under reduced pressure
  4. temperatureThe mixture was refluxed for 17 h under Argon
  5. extractionextracted with ethyl acetate
  6. customPurification by chromatography

Sources & evidence

ORD record
ord-473f15d3152d4cb6b61fa8db3a5f3858
Source dataset
uspto-grants-2008_09
Patent number
US07423181B2

Linked notes

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