Water → HCID 69135137, compound

HRID 969526Notes

Reaction equation

HRID 969526 reaction equation
[CH2:1]([O:8][C:9]1[C:17]2[N:16]=[C:15]([C:18]([F:21])([F:20])[F:19])[N:14](O)[C:13]=2[CH:12]=[C:11]([Br:23])[CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.P(Br)(Br)Br.O.C(=O)(O)[O-].[Na+]>C(Cl)(Cl)Cl>[CH2:1]([O:8][C:9]1[C:17]2[N:16]=[C:15]([C:18]([F:21])([F:19])[F:20])[NH:14][C:13]=2[CH:12]=[C:11]([Br:23])[CH:10]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 4

HCID 962WaterHCID 24614Phosphorus tribromideHCID 516892Sodium BicarbonateHCID 69134272HCID 69134272, compound

Product 1

HCID 69135137HCID 69135137, compoundYield 79.2%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

To a suspension of 26.1 g (67.4 mmol) 4benzyloxy-6-bromo-2-trifluoromethyl-benzimidazol-1-ol in chloroform (260 ml) were cautiously added 19 ml (202 mmol) phosphorus tribromide and the reaction was refluxed for 4 h. After cooling to room temperature, the reaction mixture was poured into water (600 ml), neutralized with sodium bicarbonate solution and extracted with dichloromethane. The organic layers were dried over magnesium sulphate and concentrated in vacuo to afford 19.8 g (79%) of the title compound as a brown oil.

Workup

  1. temperaturethe reaction was refluxed for 4 h
  2. extractionextracted with dichloromethane
  3. dry with materialThe organic layers were dried over magnesium sulphate
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-a24bb95439684f34aeeb01c5fe01511f
Source dataset
uspto-grants-2007_12
Patent number
US07307084B2

Reaction notes

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