(1-((2,6-Difluorophenyl)methyl)-4-methylbenzimidazol-2-yl)methan-1-ol → 1H-Benzimidazole, 1-((2,6-difluorophenyl)methyl)-4-methyl-

HRID 841529Notes

Reaction equation

HRID 841529 reaction equation
[F:1][C:2]1[CH:20]=[CH:19][CH:18]=[C:17]([F:21])[C:3]=1[CH2:4][N:5]1[C:9]2[CH:10]=[CH:11][CH:12]=[C:13]([CH3:14])[C:8]=2[N:7]=[C:6]1CO.[O-][Mn](=O)(=O)=O.[K+]>OS(O)(=O)=O>[F:1][C:2]1[CH:20]=[CH:19][CH:18]=[C:17]([F:21])[C:3]=1[CH2:4][N:5]1[C:9]2[CH:10]=[CH:11][CH:12]=[C:13]([CH3:14])[C:8]=2[N:7]=[CH:6]1

Participants

4

Reactant 2

HCID 468845(1-((2,6-Difluorophenyl)methyl)-4-methylbenzimidazol-2-yl)methan-1-ol2×HCID 516875Potassium Permanganate

Product 1

HCID 4688431H-Benzimidazole, 1-((2,6-difluorophenyl)methyl)-4-methyl-Yield 80%

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidSolvent

Procedure

In this Example, 1-(2,6-difluorobenzyl)-4-methylbenzimidazole (49) was prepared according to Method D. To 1-(2,6-difluorobenzyl)-2-hydroxymethyl-4-methylbenzimidazole (Example 40) (1.82 g, 4.52 mmol) dissolved in 1.5 M H2SO4 (40 mL) was added KMnO4 (1.50 g, 9.49 mmol, 160 M%). After 1 h at room temperature, the reaction mixture was filtered and washed with water. The brown solid was collected, suspended in acetone/methanol and filtered. The filtrate was collected and purified by flash chromatography eluting with 10% MeOH/CH2Cl2 increasing to 50% MeOH/CH2Cl2 to produce 1.42 g (4.70 mmol, 80% yield) of white powder. 1H-NMR (200 MHz, CD2Cl2): δ7.99 (br s, 1H, H2), 7.37 (br d, J=7.9 Hz, 1H, H7), 7.32 (m, 1H, H4″), 7.17 (dd, J=7.3, 7.9 Hz, 1H, H6), 7.03 (d, J=3.2 Hz, 1H, H5), 6.96 (m, 2H, H3″,5″,), 5.40 (s, 2H, CH2PhF2), 2.59 (s, 3H, CH3).

Workup

  1. filtrationthe reaction mixture was filtered
  2. washwashed with water
  3. customThe brown solid was collected
  4. filtrationfiltered
  5. customThe filtrate was collected
  6. custompurified by flash chromatography
  7. washeluting with 10% MeOH/CH2Cl2 increasing to 50% MeOH/CH2Cl2

Sources & evidence

ORD record
ord-44c33e08261944d8979cdd1aeb30bed5
Source dataset
uspto-grants-2002_04
Patent number
US06369235B1

Reaction notes

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