p-Bromochlorobenzene → 1-Chloro-4-(4-methoxyphenoxy)benzene

HRID 1909620Notes

Reaction equation

HRID 1909620 reaction equation
C(=O)([O-])[O-].[Cs+].[Cs+].Br[C:8]1[CH:13]=[CH:12][C:11]([Cl:14])=[CH:10][CH:9]=1.[CH3:15][O:16][C:17]1[CH:22]=[CH:21][C:20]([OH:23])=[CH:19][CH:18]=1>O1CCOCC1.Cl.CN(C)CC(O)=O>[CH3:15][O:16][C:17]1[CH:22]=[CH:21][C:20]([O:23][C:8]2[CH:13]=[CH:12][C:11]([Cl:14])=[CH:10][CH:9]=2)=[CH:19][CH:18]=1

Participants

6

Reactant 3

HCID 7806p-BromochlorobenzeneHCID 90154-MethoxyphenolHCID 10796Cesium carbonate

Product 1

HCID 101054561-Chloro-4-(4-methoxyphenoxy)benzeneYield 114.8%

Reagents, catalysts & solvents 2

HCID 75605N,N-Dimethylglycine hydrochlorideCatalystHCID 312751,4-DioxaneSolvent

Procedure

Following the general procedure for Example 12 (step 1), N,N-dimethylglycine hydrochloride (0.04 g, 0.26 mmol), cesium carbonate (1.85 g, 5.68 mmol), and Cu(I) iodide (0.02 g, 0.11 mmol) were added to a solution of 4-bromochlorobenzene (0.82 g, 4.28 mmol) and 4-methoxyphenol (0.35 g, 2.82 mmol) in dioxane (10 mL) to afford the title compound (0.76 g, 100%) as a brown oil.

Sources & evidence

ORD record
ord-846201a5cd4f456385d258418193f304
Source dataset
uspto-grants-2013_12
Patent number
US08598359B2

Reaction notes

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