Tetrahydrofuran → HCID 21265716, compound

HRID 566517Notes

Reaction equation

HRID 566517 reaction equation
[NH:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[N:2]1.CC([O-])(C)C.[K+].C1COCC1.[F:21][C:22]1[CH:23]=[C:24]([CH:27]=[CH:28][C:29]=1[F:30])[CH2:25]Br>CN(C=O)C.O>[F:21][C:22]1[CH:23]=[C:24]([CH:27]=[CH:28][C:29]=1[F:30])[CH2:25][N:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[N:2]1

Participants

7

Reactant 4

HCID 8028TetrahydrofuranHCID 5814364-(Bromomethyl)-1,2-difluorobenzeneHCID 23665647Potassium tert-butoxideHCID 178418385HCID 178418385, compound

Product 1

HCID 21265716HCID 21265716, compoundYield 65%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

To a solution of benzotriazole (1.2 g, 10.1 mmol) in DMF (40 mL) at r.t. was added a solution of 1M t-BuOK in THF (11 mL, 11 mmol). After stirring for 30 min., 3,4-difluorobenzyl bromide (2.4 g, 11.6 mmol) was added. The mixture was further stirred for 1 h, diluted with H2O, extracted with EtOAc. The EtOAc extract was washed H2O (3×), dried (MgSO4) and concentrated. The residue was chromatographed over silica gel and eluted with hexanes:EtOAc (3:1), then (2:1) to afford 1.6 g (65%) of title compound as a white solid.

Workup

  1. stirringThe mixture was further stirred for 1 h
  2. extractionextracted with EtOAc
  3. extractionThe EtOAc extract
  4. washwas washed H2O (3×)
  5. dry with materialdried (MgSO4)
  6. concentrationconcentrated
  7. customThe residue was chromatographed over silica gel
  8. washeluted with hexanes:EtOAc (3:1)

Sources & evidence

ORD record
ord-3dc44bdd721f4567ab07b56cb74ee569
Source dataset
uspto-grants-2001_01
Patent number
US06174874B1

Reaction notes

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