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

HRID 556037Notes

Reaction equation

HRID 556037 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([C:9](=[O:21])[CH2:10][CH2:11][C:12]2[CH:17]=[CH:16][C:15]([N+:18]([O-:20])=[O:19])=[CH:14][CH:13]=2)=[CH:5][CH:4]=1.[Br-:22]>[Al+3].[Cl-].[Cl-].[Cl-]>[Br:22][CH:10]([CH2:11][C:12]1[CH:17]=[CH:16][C:15]([N+:18]([O-:20])=[O:19])=[CH:14][CH:13]=1)[C:9]([C:6]1[CH:7]=[CH:8][C:3]([O:2][CH3:1])=[CH:4][CH:5]=1)=[O:21]

Participants

4

Reactant 2

HCID 259Bromide ionHCID 665542091-(4-Methoxy-phenyl)-3-(4-nitro-phenyl)-propan-1-one

Product 1

HCID 866366252-Bromo-1-(4-methoxy-phenyl)-3-(4-nitro-phenyl)-propan-1-oneYield 96.1%

Reagents, catalysts & solvents 1

HCID 6451240Aluminum(III) ChlorideCatalyst

Procedure

A procedure similar to step 3 of Example 1 was used, 1-(4-methoxy-phenyl)-3-(4-nitro-phenyl)-propan-1-one prepared in the step 3 and bromide were used as starting materials, and anhydrous AlCl3 was used as catalyst, the obtained product was white crystal in a yield of 96.1%, mp: 120-122 └. 1H-NMR (CDCl3, 400 MHz) δ: 3.46 (1H, dd, J=14.28, 7.28 Hz), 3.74 (1H, dd, J=14.28, 7.28 Hz), 3.88 (3H, s, OCH3), 5.27 (1H, t, J=7.28 Hz, CHBr), 6.94 (2H, d, J=8.96 Hz, ArH), 7.46 (2H, d, J=8.60 Hz, ArH), 7.96 (2H, d, J=8.96 Hz, ArH), 8.16 (2H, d, J=8.60 Hz, ArH); ESI-MS: 366.1 (M+2, 93), 364.2 (M, 100).

Sources & evidence

ORD record
ord-4913b14913054e59b610a2fbd6264d44
Source dataset
uspto-grants-2011_11
Patent number
US08053581B2

Reaction notes

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