4-Nitrobenzyl alcohol → 4-NITROBENZYLFLUORIDE

HRID 851073Notes

Reaction equation

HRID 851073 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)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 12797938HCID 12797938, compound

Product 1

HCID 108665664-NITROBENZYLFLUORIDEYield 76.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of 0.77 g (5 mmol) of 4-nitrobenzyl alcohol in 15 ml of methylene chloride was added dropwise over a period of 10 min to a stirred solution of 2.0 g (7.8 mmol) of 2,2,2-trifluoro-1-(trifluoromethyl)ethoxysulfur trifluoride in 5 ml of methylene chloride cooled to 10°. The reaction mixture was warmed to room temperature and then evaporated to dryness under reduced pressure. The residue was recrystallized from pentane to give 0.59 g (76%) of 4-nitrobenzyl fluoride as colorless needles: mp 33° to 34°. Recrystallization from pentane raised to melting point to 36° to 37°.

Workup

  1. temperaturecooled to 10°
  2. customevaporated to dryness under reduced pressure
  3. customThe residue was recrystallized from pentane

Sources & evidence

ORD record
ord-442d3898d7b24b4984093f8a814ba7e0
Source dataset
uspto-grants-1983_05
Patent number
US04382891

Reaction notes

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