Benzyl Alcohol → 2-(Benzyloxy)-1,3-difluoro-5-nitrobenzene

HRID 450434Notes

Reaction equation

HRID 450434 reaction equation
C(=O)([O-])[O-].[K+].[K+].[F:7][C:8]1[CH:13]=[C:12]([N+:14]([O-:16])=[O:15])[CH:11]=[C:10]([F:17])[C:9]=1F.[CH2:19]([OH:26])[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1>CN(C)C=O>[CH2:19]([O:26][C:9]1[C:10]([F:17])=[CH:11][C:12]([N+:14]([O-:16])=[O:15])=[CH:13][C:8]=1[F:7])[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1

Participants

5

Reactant 3

HCID 244Benzyl AlcoholHCID 11430Potassium CarbonateHCID 27827931,2,3-Trifluoro-5-nitrobenzene

Product 1

HCID 231303422-(Benzyloxy)-1,3-difluoro-5-nitrobenzeneYield 71%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Potassium carbonate (7.8 g, 56.4 mmol) was added to a solution of 1,2,3-trifluoro-5-nitrobenzene (5 g, 28.2 mmol) and benzyl alcohol (3.2 g, 29.6 mmol) in N,N-dimethylformamide (70 mL). The resultant mixture was stirred at RT overnight. The reaction mixture was concentrated under reduced pressure and the residue was partitioned between ethyl acetate and water. The organic layer was separated and washed with brine, dried (Na2SO4), concentrated under reduced pressure and purified by column chromatography to give 2-(benzyloxy)-1,3-difluoro-5-nitrobenzene (5.3 g, 71% yield). 1H NMR (400 MHz, DMSO-d6): δ 8.15 (d, J=8.4 Hz, 2H), 7.46-7.37 (m, 5H), 5.39 (s, 2H).

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. customthe residue was partitioned between ethyl acetate and water
  3. customThe organic layer was separated
  4. washwashed with brine
  5. dry with materialdried (Na2SO4)
  6. concentrationconcentrated under reduced pressure
  7. custompurified by column chromatography

Sources & evidence

ORD record
ord-7bc41a100204499fba492195a50c09df
Source dataset
uspto-grants-2013_07
Patent number
US08486951B2

Reaction notes

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