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

HRID 1670319Notes

Reaction equation

HRID 1670319 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>[F:9][C:5]1[CH:4]=[C:3]([N+:10]([O-:12])=[O:11])[C:2]([F:1])=[CH:7][C:6]=1[O:20][CH2:13][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 92%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
4 °C

Procedure

A mixture of 2,4,5-trifluoronitrobenzene (5.4 g, 30.8 mmol), benzylalcohol (3.2 mL, 30.8 mmol) and potassium carbonate (6.4 g, 46.1 mmol), in DMF (20 mL), was stirred at ambient temperature for 72 h. Water (60 mL) was added and the mixture was cooled at 4° C. for 24 h. The resultant precipitate was filtered, rinsed with water and dried in vacuo to afford the product (7.5 g, 92%) as a pale yellow solid. 1H NMR (CDCl3) δ 7.90-7.94 (m, 1H), 7.38-7.44 (m, 5H), 6.85-6.90 (m, 1H), 5.22 (s, 2H).

Workup

  1. filtrationThe resultant precipitate was filtered
  2. washrinsed with water
  3. customdried in vacuo

Sources & evidence

ORD record
ord-26cae8d94a044e9e8ca1b63b74eda745
Source dataset
uspto-grants-2011_08
Patent number
US07989477B2

Reaction notes

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