Benzyl Alcohol → 1-(Benzyloxy)-2,3-difluoro-4-nitrobenzene

HRID 2042072Notes

Reaction equation

HRID 2042072 reaction equation
F[C:2]1[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[C:4]([F:11])[C:3]=1[F:12].[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:2]1[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[C:4]([F:11])[C:3]=1[F:12])[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1

Participants

6

Reactant 4

HCID 244Benzyl AlcoholHCID 962WaterHCID 11430Potassium CarbonateHCID 698711,2,3-Trifluoro-4-nitrobenzene

Product 1

HCID 574708771-(Benzyloxy)-2,3-difluoro-4-nitrobenzeneYield 36%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 1,2,3-trifluoro-4-nitro-benzene (30 g, 0.17 mol) and benzyl alcohol (18.4 g, 0.17 mol) in DMF (300 mL) was treated with K2CO3 (35 g, 0.25 mol) and the resulting mixture was stirred at RT for 8 h. Water (300 mL) was added, and the mixture was extracted with EtOAc (3×500 mL). The combined organics were washed with brine, dried (MgSO4), concentrated in vacuo and chromatographed on silica gel to give 1-benzyloxy-2,3-difluoro-4-nitrobenzene (16 g, 36% yield). 1H NMR (400 MHz, DMSO-d6): δ 8.06 (m, 1H), 7.49-7.30 (m, 6H), 5.37 (s, 2H).

Workup

  1. extractionthe mixture was extracted with EtOAc (3×500 mL)
  2. washThe combined organics were washed with brine
  3. dry with materialdried (MgSO4)
  4. concentrationconcentrated in vacuo
  5. customchromatographed on silica gel

Sources & evidence

ORD record
ord-fc62a158958441908b90b18c152a3ddb
Source dataset
uspto-grants-2013_11
Patent number
US08586565B2

Reaction notes

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