Bromide ion → 2-Bromo-1-(4-methoxy-phenyl)-4-phenyl-butan-1-one

HRID 556093Notes

Reaction equation

HRID 556093 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([C:9](=[O:19])[CH2:10][CH2:11][CH2:12][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)=[CH:5][CH:4]=1.[Br-:20]>[Al+3].[Cl-].[Cl-].[Cl-]>[Br:20][CH:10]([CH2:11][CH2:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)[C:9]([C:6]1[CH:5]=[CH:4][C:3]([O:2][CH3:1])=[CH:8][CH:7]=1)=[O:19]

Participants

4

Reactant 2

HCID 259Bromide ionHCID 445894361-(4-Methoxyphenyl)-4-phenylbutan-1-one

Product 1

HCID 866366332-Bromo-1-(4-methoxy-phenyl)-4-phenyl-butan-1-oneYield 89.4%

Reagents, catalysts & solvents 1

HCID 6451240Aluminum(III) ChlorideCatalyst

Procedure

A procedure similar to step 3 of Example 1 was used. 1-(4-methoxy-phenyl)-4-phenyl-butan-1-one prepared in the step 2 and bromide were used as starting materials, and anhydrous AlCl3 was used as catalyst. The crude product obtained was recrystallized with a mixture of petroleum ether and ethyl acetate (2:1) to give a product as a white solid in a yield of 89.4%, mp: 65-66 └. 1H-NMR (CDCl3, 400 MHz) δ: 2.38˜2.52 (2H, m, CH2), 2.75˜2.90 (2H, m, CH2), 3.88 (3H, s, OCH3), 5.03 (1H, t, J=8.00 Hz, CHBr), 6.93 (2H, d, J=9.2 Hz, ArH), 7.18˜7.32 (5H, m, ArH), 7.91 (2H, d, J=9.20 Hz, ArH); ESI-MS m/e (%): 334.0 (M+2, 1), 332.0 (M, 1), 229.9 (53), 227.9 (53), 135.0 (100).

Workup

  1. customThe crude product obtained
  2. customwas recrystallized with a mixture of petroleum ether and ethyl acetate (2:1)

Sources & evidence

ORD record
ord-2f301e3ef7fa44d6af8a65b5e445f60c
Source dataset
uspto-grants-2011_11
Patent number
US08053581B2

Reaction notes

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