Sodium Bicarbonate → HCID 67496677, compound

HRID 1628317Notes

Reaction equation

HRID 1628317 reaction equation
[CH3:1][C:2]1[CH:7]=[C:6]([C:8]2[CH:9]=[C:10](N)[CH:11]=[C:12]([N+:14]([O-:16])=[O:15])[CH:13]=2)[CH:5]=[CH:4][N:3]=1.B(Br)(Br)Br.C(Cl)Cl.C([O-])(O)=[O:26].[Na+]>CO>[CH3:1][C:2]1[CH:7]=[C:6]([C:8]2[CH:9]=[C:10]([OH:26])[CH:11]=[C:12]([N+:14]([O-:16])=[O:15])[CH:13]=2)[CH:5]=[CH:4][N:3]=1

Participants

5

Reactant 3

HCID 516892Sodium BicarbonateHCID 22277759Boron tribromide dichloromethaneHCID 67497043HCID 67497043, compound

Product 1

HCID 67496677HCID 67496677, compoundYield 68%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To 0° C. flask charged with 65.B (2.85 g, 11.7 mmol) was added a solution of BBr3/CH2Cl2 (1.0 M, 25 mL). The solution was allowed to warm to rt and stirred for 45 mins. The resulting mixture was treated with MeOH (7 mL), neutralized with solid NaHCO3 to PH=7 and concentrated under reduced pressure. Purification of the residue by flash chromatography on silica gel using 0-10% of MeOH/CH2Cl2 for elution gave the title product 65.C as solid (1.83 g, 68%).

Workup

  1. concentrationconcentrated under reduced pressure
  2. customPurification of the residue by flash chromatography on silica gel using 0-10% of MeOH/CH2Cl2
  3. washfor elution

Sources & evidence

ORD record
ord-02bbece000814576a64bc6d72757e3b5
Source dataset
uspto-grants-2014_07
Patent number
US08785468B2

Reaction notes

Loading…