N-(3-fluoro-2-formyl-phenyl)-acetamide → N-[3-fluoro-2-(hydroxyl-o-tolyl-methyl)-phenyl]-acetamide

HRID 1294567Notes

Reaction equation

[F:1][C:2]1[C:3]([CH:12]=[O:13])=[C:4]([NH:8][C:9](=[O:11])[CH3:10])[CH:5]=[CH:6][CH:7]=1.[C:14]1([CH3:22])[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=1[Mg]Br>O1CCCC1.C(OCC)C>[F:1][C:2]1[C:3]([CH:12]([OH:13])[C:15]2[CH:16]=[CH:17][CH:18]=[CH:19][C:14]=2[CH3:22])=[C:4]([NH:8][C:9](=[O:11])[CH3:10])[CH:5]=[CH:6][CH:7]=1

Participants

Conditions

Temperature: -78 °C

Procedure

100 mg (0.83 mmol) N-(3-fluoro-2-formyl-phenyl)-acetamide are dissolved in 4 ml of tetrahydrofuran and cooled to −78° C. Then at this temperature 1.66 ml (3.3 mmol) of a 2 M solution of o-tolylmagnesium bromide in diethyl ether are added. This reaction mixture is thawed to ambient temperature overnight with stirring. Then the reaction mixture is stirred into 30 ml dist. water and extracted three times with 10 ml of ethyl acetate. The organic phase is dried with MgSO4, the solvent is eliminated in vacuo. The crude product is purified by column chromatography. The carrier material used is silica gel and the eluant used is a mixture of cyclohexane:ethyl acetate (80:20).

Workup

stirringThen the reaction mixture is stirred into 30 ml dist
extractionwater and extracted three times with 10 ml of ethyl acetate
dry with materialThe organic phase is dried with MgSO4
customThe crude product is purified by column chromatography
additiona mixture of cyclohexane:ethyl acetate (80:20)

Sources & evidence

ORD record: ord-db1a1fd68485452d9be4959907fbf2e0
Source dataset: uspto-grants-2007_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07241769B2

Reaction notes

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