4-Iodoanisole → 1-(4'-Methoxy-2-nitro-[1,1'-biphenyl]-4-yl)ethanone

HRID 1460889Notes

Reaction equation

I[C:2]1[CH:7]=[CH:6][C:5]([O:8][CH3:9])=[CH:4][CH:3]=1.[CH3:10][C:11]([C:13]1[CH:18]=[CH:17][C:16](Br)=[C:15]([N+:20]([O-:22])=[O:21])[CH:14]=1)=[O:12].CCCCCC.C(OCC)(=O)C>ClCCl.[Cu]>[C:11]([C:13]1[CH:18]=[CH:17][C:16]([C:2]2[CH:7]=[CH:6][C:5]([O:8][CH3:9])=[CH:4][CH:3]=2)=[C:15]([N+:20]([O-:22])=[O:21])[CH:14]=1)(=[O:12])[CH3:10]

Participants

Conditions

Temperature: 80 °C

Procedure

A stirred mixture of 4-iodoanisole (43.65 g, 0.187 mole), 4-bromo-3-nitro acetophenone (40.6 g, 0.166 mole) and copper powder (copper bronze, 36 g, 0.567 mole) kept under nitrogen is placed in an oil bath heated at 80° C. The temperature is slowly raised to 110° C. and the mixture is kept at this temperature for 5 days (TLC, 8:2 hexane-ethyl acetate). Upon cooling the mixture is dissolved in dichloromethane and filtered through a Celite pad. The filtrate and washings are evaporated and the residual thick, dark brown oil (58.4 g) is flash chromatographed (on silica Merck 60, preabsorbed in dichloromethane, eluted with 9:1 hexane-ethyl acetate to remove the impurities and 8:2 hexane-ethyl acetate to recover the main product) to provide 16.2 g (32%) of the title compound (yellow solid, m.p. 124°-126° C.).

Workup

customis placed in an oil bath
temperatureThe temperature is slowly raised to 110° C.
temperatureUpon cooling the mixture
filtrationfiltered through a Celite pad
customThe filtrate and washings are evaporated
customchromatographed (on silica Merck 60
custompreabsorbed in dichloromethane
washeluted with 9:1 hexane-ethyl acetate
customto remove the impurities and 8:2 hexane-ethyl acetate
customto recover the main product)

Sources & evidence

ORD record: ord-9994d1abe8654694a2bb953ee66a37ad
Source dataset: uspto-grants-1991_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05071988

Reaction notes

Loading…