Bromide ion → 2-bromo-1-(4-methoxyphenyl)propan-1-one

HRID 556086Notes

Reaction equation

HRID 556086 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([C:9](=[O:12])[CH2:10][CH3:11])=[CH:5][CH:4]=1.[Br-:13]>[Al+3].[Cl-].[Cl-].[Cl-]>[Br:13][CH:10]([CH3:11])[C:9]([C:6]1[CH:7]=[CH:8][C:3]([O:2][CH3:1])=[CH:4][CH:5]=1)=[O:12]

Participants

4

Reactant 2

HCID 259Bromide ionHCID 671444-Propanoylanisole

Product 1

HCID 2991022-bromo-1-(4-methoxyphenyl)propan-1-oneYield 90.7%

Reagents, catalysts & solvents 1

HCID 6451240Aluminum(III) ChlorideCatalyst

Procedure

A procedure similar to step 3 of Example 1 was used. 1-(4-methoxy-phenyl)-propan-1-one prepared in the step 2 and bromide were used as starting materials, and anhydrous AlCl3 was used as catalyst. A white solid product was obtained in a yield of 90.7%, mp: 69-70 └. 1H-NMR (CDCl3, 400 MHz) δ: 1.89 (3H, d, J=6.44 Hz, CHBrCH3), 3.88 (3H, s, OCH3), 5.27 (1H, q, J=6.44 Hz, CHBrCH3), 6.96 (2H, d, J=8.72 Hz, ArH), 8.02 (2H, d, J=8.72 Hz, ArH); ESI-MS m/e (%): 242.0 (M+2, 11), 241.0 (M, 11), 135.0 (100).

Workup

  1. customA white solid product was obtained in a yield of 90.7%, mp

Sources & evidence

ORD record
ord-e2614f2fd0d4497f9b118dacd278edc1
Source dataset
uspto-grants-2011_11
Patent number
US08053581B2

Reaction notes

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