3-Fluorophenylhydrazine hydrochloride → 1-Azido-3-fluorobenzene

HRID 2267132Notes

Reaction equation

HRID 2267132 reaction equation
[N:1]([O-])=O.[Na+].Cl.[F:6][C:7]1[CH:8]=[C:9]([NH:13][NH2:14])[CH:10]=[CH:11][CH:12]=1>O.Cl.C(OCC)C>[N:13]([C:9]1[CH:10]=[CH:11][CH:12]=[C:7]([F:6])[CH:8]=1)=[N+:14]=[N-:1]

Participants

6

Reactant 2

HCID 27239143-Fluorophenylhydrazine hydrochlorideHCID 23668193Sodium Nitrite

Product 1

HCID 38135191-Azido-3-fluorobenzeneYield 59.8%

Reagents, catalysts & solvents 3

HCID 313Hydrochloric AcidSolventHCID 962WaterSolventHCID 3283Diethyl EtherSolvent2×

Procedure

Sodium nitrite (262 mg) dissolved in 1.0 ml of water was dropped, under cooling with ice, into a solution of 500 mg of 3-fluorophenylhydrazine hydrochloride in 2.5 ml of concentrated hydrochloric acid and 3.0 ml of diethyl ether. 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 252 mg of the title compound as a brown oily crude product.

Workup

  1. additionwas dropped
  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-bb24a958551142f1b53d0267ccc8e017
Source dataset
uspto-grants-2010_12
Patent number
US07858800B2

Reaction notes

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