Iodoethane → 1-Ethoxy-4-fluoro-5-iodo-2-methoxybenzene

HRID 1438135Notes

Reaction equation

[F:1][C:2]1[C:7]([I:8])=[CH:6][C:5]([OH:9])=[C:4]([O:10][CH3:11])[CH:3]=1.[CH2:12](I)[CH3:13].C([O-])([O-])=O.[K+].[K+]>CN(C=O)C.C(OCC)C>[CH2:12]([O:9][C:5]1[CH:6]=[C:7]([I:8])[C:2]([F:1])=[CH:3][C:4]=1[O:10][CH3:11])[CH3:13]

Participants

Conditions

Temperature: 40 °C

Procedure

A mixture of 64C (580 mg, 2.16 mmol), ethyl iodide (0.23 mL, 2.92 mmol) and K2CO3 (598 mg, 4.32 mmol) in DMF (5.0 mL) was heated at 40° C. for 3.0 h. It was diluted with diethyl ether, washed with brine and dried over Na2SO4. After evaporation of the solvent, the crude product was purified by silica gel chromatography (EtOAc:hexanes=1:5) to give 64D (540 mg, 85% yield) as a white solid. 1H NMR (400 MHz, CDCl3) δ ppm 1.42 (t, J=7.03 Hz, 3H) 3.82 (s, 3H) 4.01 (q, J=7.03 Hz, 2H) 6.64 (d, J=9.23 Hz, 1H) 7.09 (d, J=6.15 Hz, 1H).

Workup

washwashed with brine
dry with materialdried over Na2SO4
customAfter evaporation of the solvent
customthe crude product was purified by silica gel chromatography (EtOAc:hexanes=1:5)

Sources & evidence

ORD record: ord-72397c95a2a0437ca592ac062cf7da80
Source dataset: uspto-grants-2009_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07622585B2

Reaction notes

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