Hydrochloric Acid → 1-(4-Fluoro-2-methyl-benzofuran-7-yl)-propan-1-ol

HRID 618721Notes

Reaction equation

Br[C:2]1[C:10]2[O:9][C:8]([CH3:11])=[CH:7][C:6]=2[C:5]([F:12])=[CH:4][CH:3]=1.[CH:13](=[O:16])[CH2:14][CH3:15].Cl>O1CCCC1>[F:12][C:5]1[C:6]2[CH:7]=[C:8]([CH3:11])[O:9][C:10]=2[C:2]([CH:13]([OH:16])[CH2:14][CH3:15])=[CH:3][CH:4]=1

Participants

Conditions

Temperature: 10 °C

Procedure

A solution of 5.75 g (25.1 mmol) of 7-bromo-4-fluoro-2-methylbenzofuran in 90 ml of tetrahydrofuran was added dropwise to a suspension of 0.625 g (27.5 mmol) of Mg in 100 ml of boiling tetrahydrofuran and the mixture was stirred at reflux for 2.5 hours. Subsequently, it was cooled to 10° C., 2.75 ml (37.5 mmol) of propionaldehyde were added dropwise thereto and the mixture was stirred for 30 minutes. The mixture was poured into 200 ml of 1N hydrochloric acid and extracted three times with 150 ml of dichloromethane. After drying over sodium sulfate concentration was carried out in a vacuum. The crude product obtained was purified by column chromatography on silica gel (dichloro-methane/hexane 4:1). 3.6 g (55%) of 1-(4-fluoro-2-methyl-benzofuran-7-yl)-propan-1-ol were obtained as a pale yellow oil.

Workup

temperatureat reflux for 2.5 hours
stirringthe mixture was stirred for 30 minutes
extractionextracted three times with 150 ml of dichloromethane
dry with materialAfter drying over sodium sulfate concentration
customThe crude product obtained
customwas purified by column chromatography on silica gel (dichloro-methane/hexane 4:1)

Sources & evidence

ORD record: ord-f36c733d391b4cd5a621cfbefcd38de5
Source dataset: uspto-grants-1999_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05955495

Reaction notes

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