Benzyl Alcohol → 1-(Benzyloxy)-2-chloro-3-fluoro-4-nitrobenzene

HRID 2279045Notes

Reaction equation

HRID 2279045 reaction equation
[Cl:1][C:2]1[C:7]([F:8])=[C:6]([N+:9]([O-:11])=[O:10])[CH:5]=[CH:4][C:3]=1F.[CH2:13]([OH:20])[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1.C([O-])([O-])=O.[K+].[K+].O>CN(C=O)C>[CH2:13]([O:20][C:3]1[CH:4]=[CH:5][C:6]([N+:9]([O-:11])=[O:10])=[C:7]([F:8])[C:2]=1[Cl:1])[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1

Participants

6

Reactant 4

HCID 244Benzyl AlcoholHCID 962WaterHCID 11430Potassium CarbonateHCID 2230803-Chloro-2,4-difluoronitrobenzene

Product 1

HCID 904268951-(Benzyloxy)-2-chloro-3-fluoro-4-nitrobenzeneYield 39%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 2-chloro-1,3-difluoro-4-nitrobenzene (80 g, 415 mmol) and benzyl alcohol (47 g, 435 mmol) in DMF (500 mL) was treated with K2CO3 (120 g, 870 mmol) and stirred at RT overnight. The mixture was poured into water, extracted with EtOAc (3×) and the combined organics were washed with brine, dried over Na2SO4, concentrated to dryness and purified via silica gel chromatography to afford 1-(benzyloxy)-2-chloro-3-fluoro-4-nitrobenzene (45 g, 39%). 1H NMR (400 MHz, DMSO-d6): δ 8.21 (t, J=9.2 Hz, 1 H), 7.49-730 (m, 6 H), 5.40 (s, 2H).

Workup

  1. extractionextracted with EtOAc (3×)
  2. washthe combined organics were washed with brine
  3. dry with materialdried over Na2SO4
  4. concentrationconcentrated to dryness
  5. custompurified via silica gel chromatography

Sources & evidence

ORD record
ord-766c2113b8124d759987a0aabf3d1c6f
Source dataset
uspto-grants-2015_09
Patent number
US09133183B2

Reaction notes

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