4-Nitrobenzyl alcohol → 4-NITROBENZYLFLUORIDE

HRID 851074Notes

Reaction equation

HRID 851074 reaction equation
[N+:1]([C:4]1[CH:11]=[CH:10][C:7]([CH2:8]O)=[CH:6][CH:5]=1)([O-:3])=[O:2].[F:12]C(F)(F)C(C(F)(F)F)OS(F)(F)OC(C(F)(F)F)C(F)(F)F>C(Cl)Cl>[N+:1]([C:4]1[CH:11]=[CH:10][C:7]([CH2:8][F:12])=[CH:6][CH:5]=1)([O-:3])=[O:2]

Participants

4

Reactant 2

HCID 692754-Nitrobenzyl alcoholHCID 12797939HCID 12797939, compound

Product 1

HCID 108665664-NITROBENZYLFLUORIDEYield 63.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of 770 mg (5 mmol) of 4-nitrobenzyl alcohol in 15 ml of methylene chloride was added dropwise to a stirred solution of 3.0 g (7.5 mmol) of bis[2,2,2-trifluoro-1-(trifluoromethyl)ethoxy]sulfur difluoride in 5 ml of methylene chloride at 25°. The reaction mixture was stirred for 18 hrs, and then evaporated to dryness under reduced pressure. The residue was recrystallized from pentane to give 490 mg (63%) of 4-nitrobenzyl fluoride as colorless needles, mp 33° to 34°. A second recrystallization raised the melting point to 36° to 37°. The 4-nitrobenzyl fluoride is a known compound useful as a chemical intermediate.

Workup

  1. customevaporated to dryness under reduced pressure
  2. customThe residue was recrystallized from pentane

Sources & evidence

ORD record
ord-0680bd0603e84136a815d3c631f75695
Source dataset
uspto-grants-1983_05
Patent number
US04382891

Reaction notes

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