3-Methoxybenzyl bromide → HCID 57825136, compound

HRID 1668767Notes

Reaction equation

HRID 1668767 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]([C:11]2[CH:12]=[C:13]([OH:17])[CH:14]=[CH:15][CH:16]=2)=[CH2:10])=[CH:5][C:4]=1[CH3:18].[CH3:19][O:20][C:21]1[CH:22]=[C:23]([CH:26]=[CH:27][CH:28]=1)[CH2:24]Br>CN(C)C=O.C(=O)([O-])[O-].[Cs+].[Cs+]>[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]([C:11]2[CH:16]=[CH:15][CH:14]=[C:13]([O:17][CH2:24][C:23]3[CH:26]=[CH:27][CH:28]=[C:21]([O:20][CH3:19])[CH:22]=3)[CH:12]=2)=[CH2:10])=[CH:5][C:4]=1[CH3:18]

Participants

5

Reactant 2

HCID 40672073-Methoxybenzyl bromideHCID 57825052HCID 57825052, compound

Product 1

HCID 57825136HCID 57825136, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 10796Cesium carbonateSolvent

Procedure

To a solution of 3-[1-(4-methoxy-3-methyl-phenyl)-vinyl]-phenol (400 mg, 1.67 mmol, 1.0 eq) in 3 mL of dry N,N-dimethylformamide, anhydrous cesium carbonate was added (1.08 g, 3.33 mmol, 2.0 eq.) and the mixture was stirred for 20 min at room temperature. After this time, 3-methoxybenzylbromide (167 mg, 0.832 mmol, 1.2 eq.) was added and the resulting mixture was further stirred for 16 hours at 50° C. The reaction mixture was examined LC-MS which showed>90% conversion to the desired product. The reaction mixture was cooled to room temperature, 10 mL of water was added and the mixture was extracted with DCM. The organic fraction was dried over sodium sulfate and the crude product was purified by flash chromatography eluting with cyclohexane/ethylacetate (100:0 to 90:10). 408 mg of clean product was obtained as colorless liquid (yield: 95%)

Workup

  1. stirringthe resulting mixture was further stirred for 16 hours at 50° C

Sources & evidence

ORD record
ord-31d26201dc1c4bebbc836473c6ddc2de
Source dataset
uspto-grants-2011_08
Patent number
US07989449B2

Reaction notes

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