Boron tribromide → HCID 57743039, compound

HRID 1896440Notes

Reaction equation

HRID 1896440 reaction equation
B(Br)(Br)Br.[Cl:5][C:6]1[N:10]([CH2:11][N:12]2[CH2:16][CH:15]([CH2:17][CH2:18][CH3:19])[CH2:14][C:13]2=[O:20])[C:9]2[CH:21]=[C:22]([O:25]C)[CH:23]=[CH:24][C:8]=2[N:7]=1.C([O-])(O)=O.[Na+]>C(Cl)Cl>[Cl:5][C:6]1[N:10]([CH2:11][N:12]2[CH2:16][CH:15]([CH2:17][CH2:18][CH3:19])[CH2:14][C:13]2=[O:20])[C:9]2[CH:21]=[C:22]([OH:25])[CH:23]=[CH:24][C:8]=2[N:7]=1

Participants

5

Reactant 3

HCID 25134Boron tribromideHCID 516892Sodium BicarbonateHCID 57743073HCID 57743073, compound

Product 1

HCID 57743039HCID 57743039, compoundYield 35.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Under argon, BBr3 (1M in CH2Cl2) (1.86 ml, 1.8645 mmol, 2 eq) is added drop wise to a solution of 1-[(2-chloro-6-methoxy-1H-benzimidazol-1-yl)methyl]-4-propylpyrrolidin-2-one 305 (0.3 g, 0.9322 mmol, 1 eq) in dry CH2Cl2 (20 ml). After 48 hours at room temperature, saturated aqueous solution of NaHCO3 (20 ml) is added. The aqueous layer is extracted with CH2Cl2 (3×20 ml) then the combined organic layers are dried on anhydrous MgSO4, filtered off and evaporated under reduced pressure. The remaining pale yellow solid is recrystallized in MeCN/H2O (9/1) to yield 102 mg of 1-[(2-chloro-6-hydroxy-1H-benzimidazol-1-yl)methyl]-4-propylpyrrolidin-2-one 320 as a white solid.

Workup

  1. extractionThe aqueous layer is extracted with CH2Cl2 (3×20 ml)
  2. dry with materialthe combined organic layers are dried on anhydrous MgSO4
  3. filtrationfiltered off
  4. customevaporated under reduced pressure
  5. customThe remaining pale yellow solid is recrystallized in MeCN/H2O (9/1)

Sources & evidence

ORD record
ord-ae7acb1fd98b47c59df40ba44406d2f9
Source dataset
uspto-grants-2013_08
Patent number
US08518943B2

Reaction notes

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