Water → HCID 12834670, compound

HRID 2410564Notes

Reaction equation

HRID 2410564 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][C:5](I)=[C:6]([CH:9]=1)[CH:7]=[O:8].[C:11]1([CH3:20])[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=1B(O)O.[F-].[Cs+].O>O1CCOCC1.CC(OC)(C)C.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>[Br:1][C:2]1[CH:9]=[C:6]([CH:7]=[O:8])[C:5]([C:12]2[CH:13]=[CH:14][CH:15]=[CH:16][C:11]=2[CH3:20])=[CH:4][CH:3]=1

Participants

8

Reactant 4

HCID 962WaterHCID 25953Cesium fluorideHCID 27332672-Methylphenyl boronic acidHCID 219738615-Bromo-2-iodobenzaldehyde

Product 1

HCID 12834670HCID 12834670, compound

Reagents, catalysts & solvents 3

HCID 178418476HCID 178418476, compoundCatalystHCID 15413tert-Butyl methyl etherSolventHCID 312751,4-DioxaneSolvent

Procedure

A mixture of 5-bromo-2-iodobenzaldehyde (3B Scientific Corp., 5.83 g, 18.8 mmol), o-tolylboronic acid (2.55 g, 18.8 mmol), cesium fluoride (8.55 g, 56.4 mmol) and bis(triphenylphosphine)palladium(II) chloride (263 mg, 0.38 mmol) was prepared in dioxane (60 mL) and water (25 mL) under nitrogen atmosphere and was heated at 50° C. for 16 hours. The reaction mixture was cooled at RT, diluted with MTBE (250 mL) and the layers were separated. The organic layer was washed with water (100 mL) and brine (100 mL). The aqueous layers were extracted with MTBE (150 mL). The organic layers were combined, dried (Na2SO4) and concentrated under vacuum. After purification by flash chromatography (silica, hexane/EtOAc), the title compound was obtained as a pale yellow solid (4.63 g, 90%). HPLC (Method A) Rt 5.6 min (Purity: 93%). 1H NMR (DMSO-d6, 300 MHz) δ 9.57 (s, 1H), 8.02 (s, 1H), 7.94 (m, 1H), 7.39-7.27 (m, 4H), 7.20 (m, 1H), 2.06 (s, 3H).

Workup

  1. customthe layers were separated
  2. washThe organic layer was washed with water (100 mL) and brine (100 mL)
  3. extractionThe aqueous layers were extracted with MTBE (150 mL)
  4. dry with materialdried (Na2SO4)
  5. concentrationconcentrated under vacuum
  6. customAfter purification by flash chromatography (silica, hexane/EtOAc)

Sources & evidence

ORD record
ord-b6a59fd79e0a4370b0cc00006b2ca583
Source dataset
uspto-grants-2014_08
Patent number
US08815919B2

Reaction notes

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