Hydrochloric Acid → 3'-Fluoro-4'-methoxy-4-acetylbiphenyl

HRID 2372254Notes

Reaction equation

HRID 2372254 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)[CH:5]=[CH:6][C:7]=1[O:8][CH3:9].[C:16](Cl)(=[O:18])[CH3:17].[Cl-].[Al+3].[Cl-].[Cl-].Cl>C(=S)=S>[C:16]([C:13]1[CH:12]=[CH:11][C:10]([C:4]2[CH:5]=[CH:6][C:7]([O:8][CH3:9])=[C:2]([F:1])[CH:3]=2)=[CH:15][CH:14]=1)(=[O:18])[CH3:17]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 6367Acetyl chlorideHCID 6451240Aluminum(III) ChlorideHCID 141221243-Fluoro-4-methoxybiphenyl

Product 1

HCID 143886483'-Fluoro-4'-methoxy-4-acetylbiphenylYield 29.3%

Reagents, catalysts & solvents 1

HCID 6348Carbon DisulfideSolvent

Procedure

Into a flask were charged 150 g (0.74 mol) of the above 3-fluoro-4-methoxy biphenyl, 1 l of carbon disulfide and 58 g (0.74 mol) of acetyl chloride, to which was added 120 g (0.90 mol) of anhydrous aluminum chloride over about 2.5 hours with stirring under ice cooling. The resulting mixture was further stirred for 2 hours and refluxed for 3 hours. After the air cooling, the reaction mixture was poured into 3 l of 1 normal hydrochloric acid. The precipitated solid was filtered and recrystallized with 2-propanol two times and with methanol to obtain 53 g (yield: 29%) of 4-acetyl-3'-fluoro-4'-methoxy biphenyl.

Workup

  1. stirringThe resulting mixture was further stirred for 2 hours
  2. temperaturerefluxed for 3 hours
  3. temperatureAfter the air cooling
  4. filtrationThe precipitated solid was filtered
  5. customrecrystallized with 2-propanol two times and with methanol

Sources & evidence

ORD record
ord-a3dbcb5132b84a06a7b5f033eee6d1a6
Source dataset
uspto-grants-1992_03
Patent number
US05098602

Reaction notes

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