4-Benzyloxy-2-bromo-5-methoxy-benzaldehyde → HCID 86590422, compound

HRID 2417394Notes

Reaction equation

HRID 2417394 reaction equation
[CH3:1][O:2][C:3](=[O:25])[C:4]1[CH:9]=[CH:8][C:7]([Sn](CCCC)(CCCC)CCCC)=[C:6]([O:23][CH3:24])[CH:5]=1.[CH2:26]([O:33][C:34]1[C:41]([O:42][CH3:43])=[CH:40][C:37]([CH:38]=[O:39])=[C:36](Br)[CH:35]=1)[C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1>C(#N)C.[Cu]I.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2]>[CH3:1][O:2][C:3]([C:4]1[CH:9]=[CH:8][C:7]([C:36]2[CH:35]=[C:34]([O:33][CH2:26][C:27]3[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=3)[C:41]([O:42][CH3:43])=[CH:40][C:37]=2[CH:38]=[O:39])=[C:6]([O:23][CH3:24])[CH:5]=1)=[O:25]

Participants

6

Reactant 2

HCID 9688404-Benzyloxy-2-bromo-5-methoxy-benzaldehydeHCID 69817207HCID 69817207, compound

Product 1

HCID 86590422HCID 86590422, compoundYield 54.3%

Reagents, catalysts & solvents 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)CatalystHCID 6342AcetonitrileSolvent

Procedure

To a stirred solution of 3-methoxy-4-tributylstannanyl-benzoic acid methyl ester (16g, 35 mmol) and 4-benzyloxy-2-bromo-5-methoxy-benzaldehyde (9.4 g, 29 mmol) in acetonitrile (150 mL) were added CuI (5.5 g, 29 mmol) and Pd(dppf)Cl2 (4.2 g, 6 mmol). The resulting mixture was refluxed for 14 h under argon and concentrated. The residue was purified by column chromatography (4:1 hexane/EtOAc) to provide 5′-benzyloxy-2′-formyl-2,4′-dimethoxy-biphenyl-4-carboxylic acid methyl ester (6.4 g, 54%).

Workup

  1. temperatureThe resulting mixture was refluxed for 14 h under argon
  2. concentrationconcentrated
  3. customThe residue was purified by column chromatography (4:1 hexane/EtOAc)

Sources & evidence

ORD record
ord-48d1f605f6e34e0cb4568bbcbb89db12
Source dataset
uspto-grants-2004_11
Patent number
US06825208B2

Reaction notes

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