Acetyl chloride → HCID 20535218, compound

HRID 1156635Notes

Reaction equation

HRID 1156635 reaction equation
[Cl-].[Al+3].[Cl-].[Cl-].[C:5](Cl)(=[O:7])[CH3:6].[Br:9][C:10]1[CH:15]=[CH:14][C:13]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)=[CH:12][CH:11]=1>ClCCl>[C:5]([C:16]1([C:13]2[CH:12]=[CH:11][C:10]([Br:9])=[CH:15][CH:14]=2)[CH:17]=[CH:18][CH:19]=[CH:20][CH2:21]1)(=[O:7])[CH3:6]

Participants

5

Reactant 3

HCID 6367Acetyl chlorideHCID 71014-BromobiphenylHCID 6451240Aluminum(III) Chloride

Product 1

HCID 20535218HCID 20535218, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent3×

Procedure

In a reaction flask under nitrogen atmosphere there was placed 26.6 g (0.2 Mol) of aluminum chloride, which was then covered with 150 ml of dichloromethane. There was then added dropwise 15.6 g (0.2 Mol) of acetyl chloride in 200 ml of dichloromethane, while cooling the reaction mixture. To this was added dropwise 23.3 g (0.1 Mol) of 4-bromobiphenyl in 200 ml of dichloromethane. The reaction mixture was allowed to warm to room temperature, and it was then heated to reflux for 4 hours, after which it was left at room temperature overnight under nitrogen atmosphere. There was then added 50 g of ice and the aqueous layer was separated. The organic layer was washed twice with 50 ml of saturated sodium chloride solution, then dried over magnesium sulfate and evaporated. The crude product was crystallized from 3:1 petroleum ether:benzene to give 16.9 g in the first crop, m.p. 126°-128° C.; and 3.9 g in the second crop.

Workup

  1. customIn a reaction flask under nitrogen atmosphere there was placed
  2. temperaturewhile cooling the reaction mixture
  3. temperatureit was then heated
  4. temperatureto reflux for 4 hours
  5. customthe aqueous layer was separated
  6. washThe organic layer was washed twice with 50 ml of saturated sodium chloride solution
  7. dry with materialdried over magnesium sulfate
  8. customevaporated
  9. customThe crude product was crystallized from 3:1 petroleum ether
  10. custombenzene to give 16.9 g in the first crop, m.p. 126°-128° C.

Sources & evidence

ORD record
ord-f708368ff0f24b809d1179083f0c70c4
Source dataset
uspto-grants-1982_06
Patent number
US04336397

Reaction notes

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