Cesium carbonate → 1-(4-(4-Isopropoxyphenoxy)-2,6-dimethylphenyl)ethanone

HRID 1465554Notes

Reaction equation

Br[C:2]1[CH:7]=[CH:6][C:5]([O:8][CH:9]([CH3:11])[CH3:10])=[CH:4][CH:3]=1.[OH:12][C:13]1[CH:18]=[C:17]([CH3:19])[C:16]([C:20](=[O:22])[CH3:21])=[C:15]([CH3:23])[CH:14]=1.Cl.CN(C)CC(O)=O.C(=O)([O-])[O-].[Cs+].[Cs+]>O1CCOCC1.[Cu](I)I.O>[CH:9]([O:8][C:5]1[CH:6]=[CH:7][C:2]([O:12][C:13]2[CH:14]=[C:15]([CH3:23])[C:16]([C:20](=[O:22])[CH3:21])=[C:17]([CH3:19])[CH:18]=2)=[CH:3][CH:4]=1)([CH3:11])[CH3:10]

Participants

Conditions

Temperature: 90 °C

Procedure

A mixture of 1-bromo-4-isopropoxybenzene (16-3, 3.02 g, 14.0 mmol), 1-(4-hydroxy-2,6-dimethylphenyl)ethanone (4-2, 3.54 g, 21.6 mmol), N,N-dimethylglycine HCl salt (0.50 g, 3.5 mmol), copper iodide (0.34 g, 1.8 mmol), and cesium carbonate (9.08 g, 27.9 mmol) in dioxane (30 mL) was heated at 90° C. for 48 h. The reaction mixture was cooled to room temperature, added with water, and extracted with EtOAc. The organic layer was washed with brine, dried over anhydrous MgSO4, concentrated under reduced pressure, and purified by column chromatography on silica gel (EtOAc:hexanes=1:20 as eluant) to give 1-(4-(4-isopropoxyphenoxy)-2,6-dimethylphenyl)ethanone (16-4, 2.07 g) as white solids in 79% yield: 1H NMR (500 MHz, CDCl3) δ 6.94 (m, 2 H), 6.87 (m, 2 H), 6.58 (s, 2 H), 4.50 (t, J=6.1 Hz, 1 H), 2.46 (s, 3 H), 2.21 (s, 6 H), 1.34 (s, 6 H), 1.26 (m, 3 H), 0.87 (m, 3 H).

Workup

temperatureThe reaction mixture was cooled to room temperature
extractionextracted with EtOAc
washThe organic layer was washed with brine
dry with materialdried over anhydrous MgSO4
concentrationconcentrated under reduced pressure
custompurified by column chromatography on silica gel (EtOAc:hexanes=1:20 as eluant)

Sources & evidence

ORD record: ord-b9814368d938440291184dbd068a0a53
Source dataset: uspto-grants-2015_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08999983B2

Reaction notes

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