Potassium Acetate → 3'-Bromo-4'-acetoxymethyl-1,1'-biphenyl-2-nitrile

HRID 1740245Notes

Reaction equation

[Br:1][C:2]1[CH:3]=[C:4]([C:10]2[C:11]([C:16]#[N:17])=[CH:12][CH:13]=[CH:14][CH:15]=2)[CH:5]=[CH:6][C:7]=1[CH2:8]Br.[C:18]([O-:21])(=[O:20])[CH3:19].[K+]>CN(C)C=O.O>[Br:1][C:2]1[CH:3]=[C:4]([C:10]2[C:11]([C:16]#[N:17])=[CH:12][CH:13]=[CH:14][CH:15]=2)[CH:5]=[CH:6][C:7]=1[CH2:8][O:21][C:18](=[O:20])[CH3:19]

Participants

Conditions

Temperature: 50 °C

Procedure

To a solution of 662 mg (1.89 mmol) of 3'-bromo-4'-bromomethyl-1,1'-biphenyl-2-nitrile (Step D) in 10 mL of dry dimethyl formamide was added 925 mg (9.43 mmol) of potassium acetate. The reaction mixture was heated at 50° C. for 2 hours then diluted with 100 mL of water. The mixture was extracted with ethyl acetate (3×100 mL). The organic extracts were combined, washed with water (100 mL), saturated aqueous sodium bicarbonate (100 mL) and brine (100 mL). The solution was dried over magnesium sulfate, filtered and the solvent removed under vacuum to give an oil which was purified by flash column chromatography on silica gel, eluting with hexanes/ethyl acetate (75:25), to afford 400 mg (64%) of the product as a white solid. 1H NMR (200 MHz, CDCl3): δ 2.14 (s, 3H), 5.22 (s, 2H), 7.4-7.8 (m, 7H). EI-MS: calculated for C16H12BrNO2 329; found 329, 331 (M+, 7%); 270, 272 (M-Br, 100%).

Workup

extractionThe mixture was extracted with ethyl acetate (3×100 mL)
washwashed with water (100 mL), saturated aqueous sodium bicarbonate (100 mL) and brine (100 mL)
dry with materialThe solution was dried over magnesium sulfate
filtrationfiltered
customthe solvent removed under vacuum
customto give an oil which
customwas purified by flash column chromatography on silica gel
washeluting with hexanes/ethyl acetate (75:25)

Sources & evidence

ORD record: ord-fbd1956d3ef349c08daf31aed261c9f5
Source dataset: uspto-grants-1999_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05968924

Reaction notes

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