Hydrochloric Acid → 1-(5-bromo-2-methoxyphenyl)ethanone

HRID 1978231Notes

Reaction equation

HRID 1978231 reaction equation
[Cl-].[Al+3].[Cl-].[Cl-].[Br:5][C:6]1[CH:11]=[CH:10][C:9]([O:12][CH3:13])=[CH:8][CH:7]=1.[C:14](Cl)(=[O:16])[CH3:15].Cl>ClCCl>[CH3:15][C:14]([C:10]1[CH:11]=[C:6]([Br:5])[CH:7]=[CH:8][C:9]=1[O:12][CH3:13])=[O:16]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 6367Acetyl chlorideHCID 77304-BromoanisoleHCID 6451240Aluminum(III) Chloride

Product 1

HCID 27570291-(5-bromo-2-methoxyphenyl)ethanone

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
0 °C

Procedure

To a slurry of 8.55 g (64.2 mmol) of aluminum chloride in 75 mL of dichloromethane cooled to 0° C. (under a blanket of argon) was added dropwise a solution of 10.0 g (53.5 mmol) of 4-bromoanisole and 4.6 mL (64.2 mmol) of acetyl chloride in 25 mL of dichloromethane. After the addition was complete, the clear yellow solution was stirred at 0° C. for 15 minutes, poured into 200 mL of 10% HCl (aq.) solution, cooled to 0° C. in an ice bath and then extracted with dichloromethane (3×200-mL portions). The organic phases were combined and then washed with water and brine, dried over MgSO4, filtered and concentrated in vacuo to give a yellow semi-solid. Purification by flash chromatography (silica, 10% ethyl acetate in hexane) gave the title compound as a white solid.

Workup

  1. additionAfter the addition
  2. temperaturecooled to 0° C. in an ice bath
  3. extractionextracted with dichloromethane (3×200-mL portions)
  4. washwashed with water and brine
  5. dry with materialdried over MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customto give a yellow semi-solid
  9. customPurification by flash chromatography (silica, 10% ethyl acetate in hexane)

Sources & evidence

ORD record
ord-0bc872ea66fd409f8e3f29ba2aba9bab
Source dataset
uspto-grants-2001_05
Patent number
US06235923B1

Reaction notes

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