Bromide ion → 2-Bromo-1-(4-fluoro-phenyl)-3-(4-nitro-phenyl)-propan-1-one

HRID 556041Notes

Reaction equation

HRID 556041 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8](=[O:20])[CH2:9][CH2:10][C:11]2[CH:16]=[CH:15][C:14]([N+:17]([O-:19])=[O:18])=[CH:13][CH:12]=2)=[CH:4][CH:3]=1.[Br-:21]>[Al+3].[Cl-].[Cl-].[Cl-]>[Br:21][CH:9]([CH2:10][C:11]1[CH:16]=[CH:15][C:14]([N+:17]([O-:19])=[O:18])=[CH:13][CH:12]=1)[C:8]([C:5]1[CH:4]=[CH:3][C:2]([F:1])=[CH:7][CH:6]=1)=[O:20]

Participants

4

Reactant 2

HCID 259Bromide ionHCID 669864931-(4-Fluoro-phenyl)-3-(4-nitro-phenyl)-propan-1-one

Product 1

HCID 866366262-Bromo-1-(4-fluoro-phenyl)-3-(4-nitro-phenyl)-propan-1-oneYield 95.3%

Reagents, catalysts & solvents 1

HCID 6451240Aluminum(III) ChlorideCatalyst

Procedure

A procedure similar to step 3 of Example 1 was used. 1-(4-fluoro-phenyl)-3-(4-nitro-phenyl)-propan-1-one prepared in the step 1 and bromide were used as starting materials, and anhydrous AlCl3 was used as catalyst, the obtained product was a pale yellow crystal in a yield of 95.3%, mp: 126-128 └. 1H-NMR (CDCl3, 400 MHz) δ: 3.47 (1H, dd, J=14.28, 7.28 Hz), 3.74 (1H, dd, J=14.28, 7.28 Hz), 5.25 (1H, t, J=7.28 Hz, CHBr), 7.15 (2H, t, 3JFH=3JHH=8.40 Hz, ArH), 7.46 (2H, d, J=8.40 Hz, ArH), 8.03 (2H, dd, 3JHH=8.72, 4JFH=5.36 Hz, ArH), 8.17 (2H, d, J=8.40 Hz, ArH); ESI-MS (negative ion): 352.2 (M−1, 54), 350.2 (M-3, 52), 256.2 (100).

Sources & evidence

ORD record
ord-b09f45a97dc14a1aa5167032ab45a3a6
Source dataset
uspto-grants-2011_11
Patent number
US08053581B2

Reaction notes

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