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

HRID 1098545Notes

Reaction equation

HRID 1098545 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

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

Workup

  1. extractionthe mixture was extracted with EtOAc (3×500 mL)
  2. washThe combined organic layers were washed with brine
  3. dry with materialdried (MgSO4)
  4. concentrationconcentrated in vacuo
  5. custompurified by column chromatography on silica gel

Sources & evidence

ORD record
ord-b20295f8c5b74161a709a18758f03556
Source dataset
uspto-grants-2012_03
Patent number
US08143293B2

Reaction notes

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