Tetrahydrofuran → 5-Bromo-1-methylbenzimidazol-7-ol

HRID 2209022Notes

Reaction equation

HRID 2209022 reaction equation
C([O:8][C:9]1[C:14]2[N:15]([CH3:18])[CH:16]=[N:17][C:13]=2[CH:12]=[C:11]([Br:19])[CH:10]=1)C1C=CC=CC=1.B(Br)(Br)Br.C1COCC1>C(Cl)Cl>[Br:19][C:11]1[CH:10]=[C:9]([OH:8])[C:14]2[N:15]([CH3:18])[CH:16]=[N:17][C:13]=2[CH:12]=1

Participants

5

Reactant 3

HCID 8028TetrahydrofuranHCID 25134Boron tribromideHCID 1178437907-(benzyloxy)-5-bromo-1-methyl-1H-benzo[d]imidazole

Product 1

HCID 1178431005-Bromo-1-methylbenzimidazol-7-ol

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of 7-(benzyloxy)-5-bromo-1-methyl-1H-benzo[d]imidazole 2.51 (157 mg, 0.495 mmol) in DCM (3 mL) at 0° C. was added a solution of 1.0M BBr3 in THF (1.1 equiv). After 1 h at 0° C., the reaction mixture was diluted with DCM and washed with sat'd NaHCO3 and then the aqueous layer was then extracted with EtOAc (3×). Combined organic layers were washed successively with water and brine and dried over anhydrous magnesium sulfate. The residue was purified by flash column chromatography (SiO2, 0% MeOH/EtOAc→10% MeOH/EtOAc) to give of 5-bromo-1-methyl-1H-benzo[d]imidazol-7-ol 2.56.

Workup

  1. washwashed with sat'd NaHCO3
  2. extractionthe aqueous layer was then extracted with EtOAc (3×)
  3. washCombined organic layers were washed successively with water and brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. customThe residue was purified by flash column chromatography (SiO2, 0% MeOH/EtOAc→10% MeOH/EtOAc)

Sources & evidence

ORD record
ord-bacf03d2c3a54c67a3dc0bf3f104a8b6
Source dataset
uspto-grants-2016_06
Patent number
US09376441B2

Reaction notes

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