Boron tribromide → HCID 59299374, compound

HRID 2235285Notes

Reaction equation

HRID 2235285 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([C:21]2[CH:26]=[CH:25][C:24]([O:27]C)=[CH:23][C:22]=2[CH3:29])[CH:5]=[CH:6][C:7]=1[CH2:8][CH:9]1[CH2:13][CH2:12][N:11]([CH:14]2[CH2:19][CH2:18][CH2:17][CH2:16][CH2:15]2)[C:10]1=[O:20].B(Br)(Br)Br.C(=O)(O)[O-].[Na+]>C(Cl)Cl>[Cl:1][C:2]1[CH:3]=[C:4]([C:21]2[CH:26]=[CH:25][C:24]([OH:27])=[CH:23][C:22]=2[CH3:29])[CH:5]=[CH:6][C:7]=1[CH2:8][CH:9]1[CH2:13][CH2:12][N:11]([CH:14]2[CH2:19][CH2:18][CH2:17][CH2:16][CH2:15]2)[C:10]1=[O:20]

Participants

5

Reactant 3

HCID 25134Boron tribromideHCID 516892Sodium BicarbonateHCID 59299478HCID 59299478, compound

Product 1

HCID 59299374HCID 59299374, compoundYield 98%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

Charge a flask with 3-(3-chloro-4′-methoxy-2′-methyl-biphenyl-4-ylmethyl)-1-cyclohexyl-pyrrolidin-2-one (Example 95) (475 mg, 1.2 mmol), dissolve in dry methylene chloride (11 mL) and cool to 0° C. under nitrogen. Add BBr3 (0.22 mL, 2.4 mmol) and stir at 0° C. for 20 minutes. Pour into saturated aqueous sodium bicarbonate and extract with methylene chloride. Dry over sodium sulfate, filter and concentrate in vacuo to yield 450 mg (98%) of the title compound. Mass spectrum (apci) m/z=398.3 (M+H).

Workup

  1. extractionextract with methylene chloride
  2. dry with materialDry over sodium sulfate
  3. filtrationfilter
  4. concentrationconcentrate in vacuo

Sources & evidence

ORD record
ord-4ccf5c372d894ee5921a01ad32244c2b
Source dataset
uspto-grants-2010_05
Patent number
US07713979B2

Reaction notes

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