3-Fluoroacetophenone → 3-(Dimethylamino)-1-(3-fluorophenyl)prop-2-en-1-one

HRID 514348Notes

Reaction equation

[F:1][C:2]1[CH:3]=[C:4]([C:8](=[O:10])[CH3:9])[CH:5]=[CH:6][CH:7]=1.[CH3:11][N:12]([CH:14](OC)OC)[CH3:13]>>[CH3:11][N:12]([CH3:14])/[CH:13]=[CH:9]/[C:8]([C:4]1[CH:5]=[CH:6][CH:7]=[C:2]([F:1])[CH:3]=1)=[O:10]

Participants

Reactant 2

HCID 99673-Fluoroacetophenone

HCID 78373Dimethylformamide dimethyl acetal

Product 1

HCID 57140753-(Dimethylamino)-1-(3-fluorophenyl)prop-2-en-1-oneYield 92%

Procedure

The title compound was prepared in 92% yield from 1-(3-fluorophenyl)ethanone and DMF-DMA according to the procedure for the preparation of Example 12, part A. 1H NMR (400 MHz, CDCl3): δ 2.93 (3H, s), 3.15 (3H, s), 5.65 (1H, d, J=12.4 Hz), 7.11-7.16 (1H, m), 7.34-7.39 (1H, m), 7.57-7.67 (2H, m), 7.81 (1H, d, J=12.4 Hz).

Sources & evidence

ORD record: ord-4d98ab79dee44c09b527e9e7b52433c2
Source dataset: uspto-grants-2015_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09107916B2

Reaction notes

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