Hydrochloric Acid → HCID 59599695, compound

HRID 2266780Notes

Reaction equation

HRID 2266780 reaction equation
[F:1][C:2]1[C:33]([F:34])=[CH:32][CH:31]=[CH:30][C:3]=1[O:4][CH2:5][C:6]1[N:7](C(C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[CH:8]=[CH:9][N:10]=1.Cl>C(O)C.C([O-])([O-])=O.[Na+].[Na+]>[F:1][C:2]1[C:33]([F:34])=[CH:32][CH:31]=[CH:30][C:3]=1[O:4][CH2:5][C:6]1[NH:10][CH:9]=[CH:8][N:7]=1

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 59599698HCID 59599698, compound

Product 1

HCID 59599695HCID 59599695, compoundYield 101.1%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 10340Sodium CarbonateSolvent

Procedure

To a stirred suspension of 2-(2,3-difluoro-phenoxymethyl)-1-trityl-1H-imidazole (230 mg) at room temperature in ethanol (2 ml) under an argon atmosphere was added 2 N HCl (3 ml). The mixture was heated to reflux and stirring was continued for 5 hours. The reaction mixture was cooled to room temperature and concentrated to leave an off-white solid. This was taken up in sat. aq. Na2CO3 and extracted with CH2Cl2/methanol 9:1. The combined organics were dried over MgSO4, filtered and concentrated. The crude product was purified by column chromatography (silica gel; gradient:CH2Cl2→CH2Cl2/methanol 9:1) to give 2-(2,3-difluoro-phenoxymethyl)-1H-imidazole (108 mg) as an off-white solid. MS 210.9 ([M+H]+)

Workup

  1. temperatureThe mixture was heated
  2. temperatureto reflux
  3. concentrationconcentrated
  4. customto leave an off-white solid
  5. extractionextracted with CH2Cl2/methanol 9:1
  6. dry with materialThe combined organics were dried over MgSO4
  7. filtrationfiltered
  8. concentrationconcentrated
  9. customThe crude product was purified by column chromatography (silica gel; gradient:CH2Cl2→CH2Cl2/methanol 9:1)

Sources & evidence

ORD record
ord-eca44d8547664c339c96a15439cdb1c4
Source dataset
uspto-grants-2010_12
Patent number
US07858653B2

Reaction notes

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