Potassium Carbonate → 2-[4-(Sec-butyloxy)-phenoxymethyl]-5-bromothiophene

HRID 1742832Notes

Reaction equation

[CH:1]([O:5][C:6]1[CH:11]=[CH:10][C:9]([OH:12])=[CH:8][CH:7]=1)([CH2:3][CH3:4])[CH3:2].C(=O)([O-])[O-].[K+].[K+].[Br:19][C:20]1[S:24][C:23]([CH2:25]Cl)=[CH:22][CH:21]=1>CN(C)C=O>[CH:1]([O:5][C:6]1[CH:7]=[CH:8][C:9]([O:12][CH2:25][C:23]2[S:24][C:20]([Br:19])=[CH:21][CH:22]=2)=[CH:10][CH:11]=1)([CH2:3][CH3:4])[CH3:2]

Participants

Conditions

Temperature: 20 °C

Procedure

6.64 g of 4-(sec-butyloxy)-phenol and 5.52 g of potassium carbonate are heated in 50 ml of anhydrous dimethylformamide for one hour at 70° C. Subsequently, 8.46 g of 5-bromo-2-chloromethylthiophene in 20 ml anhydrous dimethylformamide is dripped in. The mixture is stirred for 6 hours at 80° C. and overnight at room temperature (about 20° C.). It is then poured into 100 ml of ice water and extracted three times with ethyl acetate, and the organic phases are dried over magnesium sulfate. The solvent is evaporated off to give a crude product which is purified by chromatography on silica gel using n-hexane/ethyl acetate (4:1) as eluant. There is obtained 6.3 g of 2-[4-(sec-butyloxy)-phenoxymethyl]-5-bromothiophene as a colorless oil.

Workup

extractionextracted three times with ethyl acetate
dry with materialthe organic phases are dried over magnesium sulfate
customThe solvent is evaporated off
customto give a crude product which
customis purified by chromatography on silica gel

Sources & evidence

ORD record: ord-dde753bee7f64e9ab135acdf81dc8335
Source dataset: uspto-grants-1994_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05342849

Reaction notes

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