4-Bromobenzoyl chloride → HCID 18434326, compound

HRID 1636758Notes

Reaction equation

HRID 1636758 reaction equation
Cl.[CH3:2][N:3]1[CH2:7][CH2:6][CH2:5][CH:4]1[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=1C1C=CC=CC=1.[Cl-].[Al+3].[Cl-].[Cl-].[Br:24][C:25]1[CH:33]=[CH:32][C:28]([C:29]([Cl:31])=[O:30])=[CH:27][CH:26]=1>C(=S)=S>[ClH:31].[Br:24][C:25]1[CH:33]=[CH:32][C:28]([C:29]([C:8]2[CH:13]=[CH:12][C:11]([C:11]3[CH:10]=[CH:9][C:8]([CH:4]4[CH2:5][CH2:6][CH2:7][N:3]4[CH3:2])=[CH:13][CH:12]=3)=[CH:10][CH:9]=2)=[O:30])=[CH:27][CH:26]=1

Participants

5

Reactant 3

HCID 685154-Bromobenzoyl chlorideHCID 6451240Aluminum(III) ChlorideHCID 18434161HCID 18434161, compound

Product 1

HCID 18434326HCID 18434326, compoundYield 30.8%

Reagents, catalysts & solvents 1

HCID 6348Carbon DisulfideSolvent2×

Procedure

350 mg of N-methyl-2-biphenylyl-pyrrolidine hydrochloride are suspended in 10 ml of carbon disulphide and treated with 341 mg of aluminium chloride. A solution of 842 mg of 4-bromo-benzoyl chloride in 3 ml of carbon disulphide is added dropwise to this viscous mass. The mixture is held at reflux for 2 hours and evaporated. The residue is triturated in toluene and then in ethyl acetate, with 90 mg of (±)(4-bromophenyl)-[4'-(1-methylpyrrolidin-2-yl)-biphenyl-4-yl]-methanone.hydrochloride, m.p. 225° C., being obtained.

Workup

  1. temperatureat reflux for 2 hours
  2. customevaporated
  3. customThe residue is triturated in toluene

Sources & evidence

ORD record
ord-0ef5d551ca7849f38951490d8d6724f6
Source dataset
uspto-grants-2000_03
Patent number
US06034275

Reaction notes

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