Anisole → (4-Iodophenyl)(4-methoxyphenyl)methanone

HRID 750009Notes

Reaction equation

[Cl-].[Al+3].[Cl-].[Cl-].[I:5][C:6]1[CH:14]=[CH:13][C:9]([C:10](Cl)=[O:11])=[CH:8][CH:7]=1.[C:15]1([O:21][CH3:22])[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1>[N+](C1C=CC=CC=1)([O-])=O>[I:5][C:6]1[CH:14]=[CH:13][C:9]([C:10]([C:18]2[CH:19]=[CH:20][C:15]([O:21][CH3:22])=[CH:16][CH:17]=2)=[O:11])=[CH:8][CH:7]=1

Participants

Conditions

Temperature: 0 °C

Procedure

Nitrobenzene (45 ml) was cooled in an ice-bath and treated portionwise with aluminum chloride (13.5 g, 101 mmol, 1.15 eq.) and followed by 4-iodobenzoic acid chloride (25 g, 94 mmol, 1.07 eq.) in nitrobenzene (25 ml) at a maximum of 10° C. The mixture was stirred at 0° C. for 10 minutes, where upon anisole (9.5 g, 88 mmol, 1 eq.) was added dropwise in such a manner that the temperature didn't excess 10° C. The solution then was left to warm to room temperature overnight. The yellow suspension was poured into ice-water (750 ml). The precipitate was collected by filtration and washed with water and then dissolved in dichloromethane (2 L), which was washed NaHCO3 (aq.) (150 ml×2), dried over MgSO4. Evaporation of solvent under reduced pressure to provide the title product in (26.7 g, 90%), 1H NMR (400 MHz, CDCl3) δ 3.89 (s, 3H), 6.96 (d, J=8.4 Hz, 2H), 7.48 (d, J=8.0 Hz, 2H), 7.79 (d, J=8.4 Hz, 2H), 7.84 (d, J=8.0 Hz, 2H);

Workup

customdidn't excess 10° C
waitThe solution then was left
temperatureto warm to room temperature overnight
filtrationThe precipitate was collected by filtration
washwashed with water
dissolutiondissolved in dichloromethane (2 L)
washwhich was washed NaHCO3 (aq.) (150 ml×2)
dry with materialdried over MgSO4
customEvaporation of solvent under reduced pressure

Sources & evidence

ORD record: ord-ad11cfd285ae48d9beb5d1abb1cd164f
Source dataset: uspto-grants-2008_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07402684B2

Reaction notes

Loading…