4-Fluorophenylhydrazine hydrochloride → 1-Azido-4-fluorobenzene

HRID 2267134Notes

Reaction equation

HRID 2267134 reaction equation
[N:1]([O-])=O.[Na+].Cl.[F:6][C:7]1[CH:12]=[CH:11][C:10]([NH:13][NH2:14])=[CH:9][CH:8]=1>O.Cl.C(OCC)C>[N:13]([C:10]1[CH:11]=[CH:12][C:7]([F:6])=[CH:8][CH:9]=1)=[N+:14]=[N-:1]

Participants

6

Reactant 2

HCID 699814-Fluorophenylhydrazine hydrochlorideHCID 23668193Sodium Nitrite

Product 1

HCID 108879741-Azido-4-fluorobenzeneYield 194%

Reagents, catalysts & solvents 3

HCID 313Hydrochloric AcidSolventHCID 962WaterSolventHCID 3283Diethyl EtherSolvent2×

Procedure

A solution of 262 mg of sodium nitrite dissolved in 2.0 ml of water was dropped into a solution of 3.09 g of 4-fluorophenylhydrazine hydrochloride in 20 ml of concentrated hydrochloric acid and 10 ml of diethyl ether under cooling with ice. Temperature of the reaction solution was raised to room temperature followed by stirring for 3 hours. The reaction solution was diluted with diethyl ether, washed with water and then with a saturated saline solution and dried over sodium sulfate. The solvent was evaporated in vacuo to give 1.01 g of the crude title compound as a brown oily substance.

Workup

  1. temperatureunder cooling with ice
  2. washwashed with water
  3. dry with materialwith a saturated saline solution and dried over sodium sulfate
  4. customThe solvent was evaporated in vacuo

Sources & evidence

ORD record
ord-1b601f47079241ce9159720bc50a4f01
Source dataset
uspto-grants-2010_12
Patent number
US07858800B2

Reaction notes

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