Boron tribromide → HCID 14576902, compound

HRID 1904621Notes

Reaction equation

HRID 1904621 reaction equation
C[O:2][C:3]1[CH:4]=[C:5]([CH:11]2[N:16]([C:17]3[CH:22]=[CH:21][C:20]([Cl:23])=[CH:19][CH:18]=3)[C:15](=[O:24])[CH2:14][CH2:13][CH2:12]2)[CH:6]=[CH:7][C:8]=1[O:9]C.B(Br)(Br)Br>C(Cl)Cl>[OH:2][C:3]1[CH:4]=[C:5]([CH:11]2[N:16]([C:17]3[CH:18]=[CH:19][C:20]([Cl:23])=[CH:21][CH:22]=3)[C:15](=[O:24])[CH2:14][CH2:13][CH2:12]2)[CH:6]=[CH:7][C:8]=1[OH:9]

Participants

4

Reactant 2

HCID 25134Boron tribromideHCID 14576875HCID 14576875, compound

Product 1

HCID 14576902HCID 14576902, compoundYield 78%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 670 mg of 6-(3,4-dimethoxyphenyl)-1-(4-chlorophenyl)-2-piperidone in 17 ml of methylene chloride was added, under ice-cooling, 1.0 ml of boron tribromide, and the mixture was stirred under ice-cooling for 1 hour and at room temperature for 45 minutes. The mixture was treated with ice-water, extracted with chloroform. The extracts were washed with water, dried, and concentrated under reduced pressure. The residue was recrystallized from ethyl acetate to give 480 mg of 6-(3,4-dihydroxyphenyl)-1-(4-chlorophenyl)-2-piperidone as colorless prisms.

Workup

  1. temperaturecooling
  2. extractionextracted with chloroform
  3. washThe extracts were washed with water
  4. customdried
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was recrystallized from ethyl acetate

Sources & evidence

ORD record
ord-04fcd331f6264f7fb5057b4daa8b89ff
Source dataset
uspto-grants-1989_06
Patent number
US04839360

Reaction notes

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