Anisole → 2-(4-Bromophenyl)-1-(4-methoxyphenyl) ethanone

HRID 1454425Notes

Reaction equation

HRID 1454425 reaction equation
[Al+3].[Cl-].[Cl-].[Cl-].[C:5]1([O:11][CH3:12])[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1.[Br:13][C:14]1[CH:19]=[CH:18][C:17]([CH2:20][C:21](Cl)=[O:22])=[CH:16][CH:15]=1>Cl>[Br:13][C:14]1[CH:19]=[CH:18][C:17]([CH2:20][C:21]([C:8]2[CH:9]=[CH:10][C:5]([O:11][CH3:12])=[CH:6][CH:7]=2)=[O:22])=[CH:16][CH:15]=1

Participants

5

Reactant 3

HCID 7519AnisoleHCID 181552Benzeneacetyl chloride, 4-bromo-HCID 6451240Aluminum(III) Chloride

Product 1

HCID 118459132-(4-Bromophenyl)-1-(4-methoxyphenyl) ethanoneYield 73%

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Procedure

To a 50 mL three-necked flask containing AlCl3 (4.406 g; 33.05 mmol) under N2, anisole (IVa) (4.467 g; 41.31 mmol) was added in one portion at RT. The reaction was exothermic. To this suspension (4-bromo-phenyl)-acetyl chloride (IIIa) (6.430 g; 27.54 mmol) was added drop wise keeping temperature below 20° C. Then the resulting red suspension was stirred at RT for 3h30. The red thick solution was poured under stirring into a mixture of ice and 1N HCl (100 mL), then the resulting white solid was filtered, and washed with water. The solid was washed with pentane (3×30 mL) and dried under vacuum at RT to give a white powder (m=8.51 g). Purification was performed by crystallization from acetone (30 ml) to give the title compound as a white powder (m=6.113 g) in a 73% yield.

Workup

  1. customtemperature below 20° C
  2. additionThe red thick solution was poured
  3. filtrationthe resulting white solid was filtered
  4. washwashed with water
  5. washThe solid was washed with pentane (3×30 mL)
  6. customdried under vacuum at RT
  7. customto give a white powder (m=8.51 g)
  8. customPurification
  9. customwas performed by crystallization from acetone (30 ml)

Sources & evidence

ORD record
ord-64458c8ebd064676816ee44bd779ff9e
Source dataset
uspto-grants-2009_01
Patent number
US07479575B2

Reaction notes

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