Fluorobenzene → 1-(4-Fluoro-phenyl)-3-(4-nitro-phenyl)-propan-1-one

HRID 556040Notes

Reaction equation

HRID 556040 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([CH2:10][CH2:11][C:12](Cl)=[O:13])=[CH:6][CH:5]=1)([O-:3])=[O:2].[F:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1>[Al+3].[Cl-].[Cl-].[Cl-]>[F:15][C:16]1[CH:21]=[CH:20][C:19]([C:12](=[O:13])[CH2:11][CH2:10][C:7]2[CH:8]=[CH:9][C:4]([N+:1]([O-:3])=[O:2])=[CH:5][CH:6]=2)=[CH:18][CH:17]=1

Participants

4

Reactant 2

HCID 10008FluorobenzeneHCID 147973603-(4-Nitrophenyl)propionyl chloride

Product 1

HCID 669864931-(4-Fluoro-phenyl)-3-(4-nitro-phenyl)-propan-1-oneYield 61.2%

Reagents, catalysts & solvents 1

HCID 6451240Aluminum(III) ChlorideCatalyst

Procedure

A procedure similar to step 2 of Example 1 was used. 3-(4-nitro-phenyl)-propionyl chloride prepared in the step 2 of Example 6 and fluorobenzene were used as starting materials, and anhydrous AlCl3 was used as catalyst. The obtained product was a white solid in a yield of 61.2%, mp: 122-124 └. 1H-NMR (CDCl3, 400 MHz) δ: 3.19 (2H, t, J=7.28 Hz), 3.32 (2H, t, J=7.28 Hz), 7.14 (2H, t, 3JFH=3JHH=8.40 Hz, ArH), 7.42 (2H, d, J=8.40 Hz, ArH), 7.99 (2H, dd, 3JHH=7.84, 4JFH=5.60 Hz, ArH), 8.16 (2H, d, J=8.40 Hz, ArH); EI-MS m/e (%): 273.1 (M+, 55), 123.0 (100).

Sources & evidence

ORD record
ord-0ae01970e9974a348ae54dd4bb9603b4
Source dataset
uspto-grants-2011_11
Patent number
US08053581B2

Reaction notes

Loading…