Water → 4-(1-ethyl-1H-benzoimidazol-2-ylmethoxy)-2-fluoro-5-methoxy-benzaldehyde

HRID 253475Notes

Reaction equation

HRID 253475 reaction equation
[NH:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[C:2]1[CH2:10][O:11][C:12]1[C:19]([O:20][CH3:21])=[CH:18][C:15]([CH:16]=[O:17])=[C:14]([F:22])[CH:13]=1.[H-].[Na+].Br[CH2:26][CH3:27].O>CN(C)C(=O)C>[CH2:26]([N:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[C:2]1[CH2:10][O:11][C:12]1[C:19]([O:20][CH3:21])=[CH:18][C:15]([CH:16]=[O:17])=[C:14]([F:22])[CH:13]=1)[CH3:27]

Participants

6

Reactant 4

HCID 962WaterHCID 6332Ethyl BromideHCID 24758Sodium hydrideHCID 580860204-(1H-benzimidazol-2-ylmethoxy)-2-fluoro-5-methoxy-benzaldehyde

Product 1

HCID 598038224-(1-ethyl-1H-benzoimidazol-2-ylmethoxy)-2-fluoro-5-methoxy-benzaldehydeYield 89%

Reagents, catalysts & solvents 1

HCID 31374DimethylacetamideSolvent

Procedure

To a solution of 4-(1H-benzoimidazol-2-ylmethoxy)-2-fluoro-5-methoxy-benzaldehyde (215, 4.0 g, 13 mmol) in N,N-dimethylacetamide (80 mL) was added sodium hydride (60% dispersion in mineral oil, 0.65 g, 16 mmol) portion wise. After the addition was complete, the reaction was stirred for 30 minutes after which bromoethane (1.2 mL, 16 mmol) was added and then allowed to stir for several hours. The reaction mixture was then poured into water (1 L) with stirring and the precipitated solid was filtered, washed with water and dried to give the desired compound (216, 3.8 g, 87% yield).

Workup

  1. additionAfter the addition
  2. additionwas added
  3. stirringwith stirring
  4. filtrationthe precipitated solid was filtered
  5. washwashed with water
  6. customdried

Sources & evidence

ORD record
ord-af7fd7be89234770830ee24e89cb90a7
Source dataset
uspto-grants-2011_01
Patent number
US07872018B2

Reaction notes

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