Sodium Chloride → HCID 23508412, compound

HRID 1883667Notes

Reaction equation

Br[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[CH2:8][C:9]#[N:10].[CH3:11][O:12][C:13]1[CH:18]=[CH:17][C:16](B(O)O)=[CH:15][CH:14]=1.C([O-])(=O)C.[K+].[Cl-].[Na+]>[Br-].C([N+](CCCC)(CCCC)CCCC)CCC.C([O-])(=O)C.[Pd+2].C([O-])(=O)C.O>[CH3:11][O:12][C:13]1[CH:18]=[CH:17][C:16]([C:2]2[C:3]([CH2:8][C:9]#[N:10])=[CH:4][CH:5]=[CH:6][CH:7]=2)=[CH:15][CH:14]=1

Participants

Conditions

Temperature: 70 °C

Procedure

A mixture composed of 392 mg of 2-bromophenylacetonitrile, 334 mg of 4-methoxyphenylboronic acid, 0.9 mg of palladium acetate, 691 mg of potassium acetate, 645 mg of tetrabutylammonium bromide, and 2.2 ml of distilled water was stirred at 70° C. for 2 hours under an atmosphere of nitrogen. After the reaction mixture was poured into a saturated aqueous solution of sodium chloride, the product was extracted with ethyl acetate The organic layer was washed with water and dried over anhydrous magnesium sulfate. After the solvent was distilled off, the resulting crude product was purified by silica gel column chromatography (using a 3:1 mixture of hexane and ethyl acetate as the eluent) to obtain 343 mg of 4′-methoxy-2-biphenylaceto-nitrile.

Workup

extractionthe product was extracted with ethyl acetate The organic layer
washwas washed with water
dry with materialdried over anhydrous magnesium sulfate
distillationAfter the solvent was distilled off
customthe resulting crude product was purified by silica gel column chromatography (
additiona 3:1 mixture of hexane and ethyl acetate as the eluent)

Sources & evidence

ORD record: ord-fe60542953b34391aa0d9a1a6b40ab99
Source dataset: uspto-grants-2004_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06762205B1

Reaction notes

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