Benzyl Alcohol → 1-(Benzyloxy)-2,5-difluoro-4-nitrobenzene

HRID 520670Notes

Reaction equation

HRID 520670 reaction equation
[F:1][C:2]1[CH:7]=[C:6](F)[C:5]([F:9])=[CH:4][C:3]=1[N+:10]([O-:12])=[O:11].[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:6]1[CH:7]=[C:2]([F:1])[C:3]([N+:10]([O-:12])=[O:11])=[CH:4][C:5]=1[F:9])[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1

Participants

6

Reactant 4

HCID 244Benzyl AlcoholHCID 962WaterHCID 11430Potassium CarbonateHCID 750121,2,4-Trifluoro-5-nitrobenzene

Product 1

HCID 574708681-(Benzyloxy)-2,5-difluoro-4-nitrobenzeneYield 74.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 2,4,5-trifluoronitrobenzene (5.4 g, 30.5 mmol) and benzyl alcohol (3.2 mL, 30.5 mmol) in DMF (20 mL) was added K2CO3 (6.33 g, 46.1 mmol). The reaction was stirred at room temperature for 72 hours. Water (60 mL) was added at 0° C. and the resulted mixture was further stirred at 4° C. for 24 hours. The solid was collected by filtration, washed with 30 mL of water, and dried in vacuo at 45° C. to provide the title compound as a pale yellow solid (6.0 g, 74%).

Workup

  1. stirringthe resulted mixture was further stirred at 4° C. for 24 hours
  2. filtrationThe solid was collected by filtration
  3. washwashed with 30 mL of water
  4. customdried in vacuo at 45° C.

Sources & evidence

ORD record
ord-b8061cc1d4ed47b9af5d325dec1ab2a8
Source dataset
uspto-grants-2016_05
Patent number
US09326975B2

Reaction notes

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