Bromide ion → 1-Hexanone, 2-bromo-1-(4-methoxyphenyl)-

HRID 556099Notes

Reaction equation

HRID 556099 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([C:9](=[O:15])[CH2:10][CH2:11][CH2:12][CH2:13][CH3:14])=[CH:5][CH:4]=1.[Br-:16]>[Al+3].[Cl-].[Cl-].[Cl-]>[Br:16][CH:10]([CH2:11][CH2:12][CH2:13][CH3:14])[C:9]([C:6]1[CH:7]=[CH:8][C:3]([O:2][CH3:1])=[CH:4][CH:5]=1)=[O:15]

Participants

4

Reactant 2

HCID 259Bromide ionHCID 808091-(4-Methoxyphenyl)hexan-1-one

Product 1

HCID 109349931-Hexanone, 2-bromo-1-(4-methoxyphenyl)-Yield 93.4%

Reagents, catalysts & solvents 1

HCID 6451240Aluminum(III) ChlorideCatalyst

Procedure

A procedure similar to step 3 of Example 1 was used. 1-(4-methoxy-phenyl)-hexan-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 distilled under a reduced pressure and purified by a silica gel column chromatography eluted with petroleum ether and ethyl acetate (20:1) to give a product as a white solid in a yield of 93.4%, mp: 54-55 └. 1H-NMR (CDCl3, 400 MHz) δ: 0.92 (3H, t, J=7.2 Hz, CH3), 1.30˜1.60 (4H, m, CH2CH2), 2.05˜2.25 (2H, m, CH2CHBr), 3.89 (3H, s, OCH3), 5.11 (1H, t, J=7.2 Hz, CHBr), 6.96 (2H, d, J=8.80 Hz, ArH), 8.01 (2H, d, J=8.80 Hz, ArH); ESI-MS m/e (%): 286.1 (M+2, 2), 284.1 (M, 2), 230.0 (3), 228.0 (3), 205.1 (5), 135.1 (100).

Workup

  1. customThe crude product obtained
  2. distillationwas distilled under a reduced pressure
  3. custompurified by a silica gel column chromatography
  4. washeluted with petroleum ether and ethyl acetate (20:1)

Sources & evidence

ORD record
ord-27e77cc7d6844ae5937bf29243533076
Source dataset
uspto-grants-2011_11
Patent number
US08053581B2

Reaction notes

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