Benzyl Alcohol → 1-(Benzyloxy)-3-fluoro-2-nitrobenzene

HRID 730558Notes

Reaction equation

HRID 730558 reaction equation
[H-].[Na+].[CH2:3]([OH:10])[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.[F:11][C:12]1[CH:17]=[CH:16][CH:15]=[C:14](F)[C:13]=1[N+:19]([O-:21])=[O:20].O>CN(C=O)C.C(OCC)(=O)C>[CH2:3]([O:10][C:14]1[CH:15]=[CH:16][CH:17]=[C:12]([F:11])[C:13]=1[N+:19]([O-:21])=[O:20])[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1

Participants

7

Reactant 4

HCID 244Benzyl AlcoholHCID 962WaterHCID 24758Sodium hydrideHCID 879221,3-Difluoro-2-nitrobenzene

Product 1

HCID 578349821-(Benzyloxy)-3-fluoro-2-nitrobenzeneYield 87%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a suspension of sodium hydride (1.522 g, 38.06 mmol) in anhydrous DMF (150 mL) at room temperature was added benzyl alcohol (3.44 mL, 33.3 mmol) dropwise over 10 minutes, and stirring was continued for another 10 minutes. 2,6-Difluoronitrobenzene (5.046 g, 31.72 mmol) was added to the reaction mixture in one portion. The reaction mixture was stirred for an hour, and 100 mL water and 100 mL ethyl acetate were added. The layers were separated, and the aqueous layer was extracted with 75 mL ethyl acetate. The combined organic layers were washed with 100 mL water and 100 mL brine, dried over sodium sulfate and concentrated in vacuo. The resulting residue was purified by flash chromatography (6% to 35% ethyl acetate in hexanes) to give 6.818 g (27.6 mmol, 87%) of 1-benzyloxy-3-fluoro-2-nitro-benzene as a yellow oil. MS: 248 (M+H)+.

Workup

  1. stirringThe reaction mixture was stirred for an hour
  2. customThe layers were separated
  3. extractionthe aqueous layer was extracted with 75 mL ethyl acetate
  4. washThe combined organic layers were washed with 100 mL water and 100 mL brine
  5. dry with materialdried over sodium sulfate
  6. concentrationconcentrated in vacuo
  7. customThe resulting residue was purified by flash chromatography (6% to 35% ethyl acetate in hexanes)

Sources & evidence

ORD record
ord-7b700593b83e420c8472593301e35ca4
Source dataset
uspto-grants-2009_09
Patent number
US07582760B2

Reaction notes

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