Boron tribromide → 1-Cyclohexyl-3-(2,6-dichloro-4-hydroxy-benzyl)-pyrrolidin-2-one

HRID 415978Notes

Reaction equation

HRID 415978 reaction equation
[CH:1]1([N:7]2[CH2:11][CH2:10][CH:9]([CH2:12][C:13]3[C:18]([Cl:19])=[CH:17][C:16]([O:20]C)=[CH:15][C:14]=3[Cl:22])[C:8]2=[O:23])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.B(Br)(Br)Br.C(=O)(O)[O-].[Na+]>ClCCl>[CH:1]1([N:7]2[CH2:11][CH2:10][CH:9]([CH2:12][C:13]3[C:18]([Cl:19])=[CH:17][C:16]([OH:20])=[CH:15][C:14]=3[Cl:22])[C:8]2=[O:23])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6]1

Participants

5

Reactant 3

HCID 25134Boron tribromideHCID 516892Sodium BicarbonateHCID 592994141-Cyclohexyl-3-(2,6-dichloro-4-methoxy-benzyl)-pyrrolidin-2-one

Product 1

HCID 592994221-Cyclohexyl-3-(2,6-dichloro-4-hydroxy-benzyl)-pyrrolidin-2-oneYield 12.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

Dissolve 1-cyclohexyl-3-(2,6-dichloro-4-methoxy-benzyl)-pyrrolidin-2-one (86 g, 241.4 mmol) in 1300 mL dichloromethane then cool to 0° C. under nitrogen. Slowly add BBr3 (120.9 g, 482.75 mmol) to the stirring cold solution keeping the internal temperature below 3.5° C. Stir the solution cold for ˜2 hours, then pour into 4 L of saturated sodium bicarbonate and stir rapidly for ˜20 minutes. Filter and wash the solid with water, then air dry on the funnel. Separate the organic portion of the filtrate and wash with water then brine. Dry over sodium sulfate, filter and concentrate under vacuum. Suspend the resultant tan solid in dichloromethane, filter, wash the solid with dichloromethane and dry to yield 10.5 g of off-white solid. Combine all solids and dry over night in a vacuum oven at 45° C. to yield 78.6 g (95%) of a light-tan solid: MS: (m/z) 342 (M+).

Workup

  1. customthe internal temperature below 3.5° C
  2. stirringstir rapidly for ˜20 minutes
  3. filtrationFilter
  4. washwash the solid with water
  5. customair dry on the funnel
  6. customSeparate the organic portion of the filtrate
  7. washwash with water
  8. dry with materialDry over sodium sulfate
  9. filtrationfilter
  10. concentrationconcentrate under vacuum
  11. filtrationfilter
  12. washwash the solid with dichloromethane
  13. customdry

Sources & evidence

ORD record
ord-8b5f8e9b51b247e6ad09f09cf313cd18
Source dataset
uspto-grants-2012_01
Patent number
US08088776B2

Reaction notes

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