Bromide ion → 2-Bromo-1-(4-methoxyphenyl)-3-phenylpropan-1-one

HRID 556030Notes

Reaction equation

HRID 556030 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([C:9](=[O:18])[CH2:10][CH2:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)=[CH:5][CH:4]=1.[Al+3].[Cl-].[Cl-].[Cl-].[Br-:23]>C(Cl)(Cl)Cl>[Br:23][CH:10]([CH2:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)[C:9]([C:6]1[CH:5]=[CH:4][C:3]([O:2][CH3:1])=[CH:8][CH:7]=1)=[O:18]

Participants

5

Reactant 3

HCID 259Bromide ion2×HCID 2455544'-Methoxy-3-phenylpropiophenoneHCID 6451240Aluminum(III) Chloride

Product 1

HCID 137372192-Bromo-1-(4-methoxyphenyl)-3-phenylpropan-1-oneYield 93.9%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent2×

Procedure

To a 500 ml three-necked flask equipped with a thermometer were added 23.0 g (95.7 mmol) 1-(4-methoxy-phenyl)-3-phenyl-propan-1-one prepared in the step 2, 0.30 g (2.25 mmol) anhydrous AlCl3 and 150 ml chloroform, the resulting mixture was agitated, upon the completion of the dissolution, to the mixture was added dropwise a bromide dissolved in 30 ml chloroform maintaining at 5-10° C. in an ice-bath, the dripping was controlled to make the color of bromide disappear quickly. Upon the completion of addition, the mixture was agitated at room temperature for 30 minutes, and then placed into a separating funnel, washed with water, then with saturated aqueous sodium bicarbonate solution, and then with water, dried over anhydrous sodium sulfate, filtrated and concentrated under a reduced pressure to a obtain a crude product, which was subjected to a silica gel column chromatography eluted with petroleum ether/ethyl acetate (13:1) to obtain a 28.7 g colorless liquid product, which was recrystallized with anhydrous ethanol to obtain a white solid in a yield of 93.9%, mp: 57-58□. 1H-NMR (CDCl3, 400 MHz) δ: 3.34 (1H, dd, J=14.28, 7.00 Hz), 3.66 (1H, dd, J=14.28, 7.00 Hz), 3.13 (3H, s, OCH3), 5.29 (1H, t, J=7.32 Hz, CHBr), 6.91 (2H, d, J=9.00 Hz, ArH), 7.18˜7.32 (5H, m, ArH), 7.94 (2H, d, J=9.00 Hz, ArH); ESI-MS m/e (%): 320.8 (M+1, 100), 239.2 (M-Br, 18).

Workup

  1. customTo a 500 ml three-necked flask equipped with a thermometer
  2. additionUpon the completion of addition
  3. stirringthe mixture was agitated at room temperature for 30 minutes
  4. customplaced into a separating funnel
  5. washwashed with water
  6. dry with materialwith saturated aqueous sodium bicarbonate solution, and then with water, dried over anhydrous sodium sulfate
  7. filtrationfiltrated
  8. concentrationconcentrated under a reduced pressure to
  9. customa obtain a crude product, which
  10. washeluted with petroleum ether/ethyl acetate (13:1)

Sources & evidence

ORD record
ord-43863487582d402f8740c55c7073cb15
Source dataset
uspto-grants-2011_11
Patent number
US08053581B2

Reaction notes

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