Hydrochloric Acid → HCID 67199474, compound

HRID 547280Notes

Reaction equation

HRID 547280 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]([CH:8]([CH3:11])[C:9]#[N:10])[CH:5]=[CH:6][CH:7]=1.N1C=CC=CC=1.[CH3:18][O:19][C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=1B(O)O.Cl>C(Cl)Cl>[CH3:18][O:19][C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=1[O:1][C:2]1[CH:3]=[C:4]([CH:8]([CH3:11])[C:9]#[N:10])[CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 1049PyridineHCID 27339582-Methoxyphenylboronic acidHCID 22615934891657-51-5

Product 1

HCID 67199474HCID 67199474, compoundYield 85%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 2-(3-hydroxyphenyl)propionitrile (0.118 g, 0.80 mmol), prepared as above described, in dry CH2Cl2 (6 mL were sequentially added, molecular sieves (4 Å), CuOAc (0.145 mg, 0.80 mmol) and pyridine (0.33 mL, 4.0 mmol). After stirring 20 min commercial 2-methoxyphenylboronic acid (0.243 g 1.60 mmol) was added. The reaction mixture was stirred overnight at room temperature. The reaction mixture was cooled to 0° C., 0.5N HCl added and the organic phase washed (3×10 mL) with 0.5N HCl. After drying over Na2SO4 and solvent evaporation under reduced pressure a residue was obtained that, after flash chromatography (eluent mixture n-hexane/EtOAc 9:1), afforded 2-{3-[(2-methoxy)phenoxy)phenyl]propionitrile as pale yellow oil (0.172 g, 0.68 mmol). Yield 85%.

Workup

  1. additionwere sequentially added
  2. additionwas added
  3. temperatureThe reaction mixture was cooled to 0° C.
  4. washthe organic phase washed (3×10 mL) with 0.5N HCl
  5. dry with materialAfter drying over Na2SO4 and solvent evaporation under reduced pressure a residue
  6. customwas obtained that, after flash chromatography (eluent mixture n-hexane/EtOAc 9:1)

Sources & evidence

ORD record
ord-83577a915412462c9f341cbb2bf92bf5
Source dataset
uspto-grants-2011_05
Patent number
US07939521B2

Reaction notes

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