Hydrazine, (2-fluorophenyl)-, hydrochloride (1:1) → 1-Azido-2-fluorobenzene

HRID 2267131Notes

Reaction equation

HRID 2267131 reaction equation
[N:1]([O-])=O.[Na+].Cl.[F:6][C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=1[NH:13][NH2:14]>O.Cl.C(OCC)C>[N:13]([C:8]1[CH:9]=[CH:10][CH:11]=[CH:12][C:7]=1[F:6])=[N+:14]=[N-:1]

Participants

6

Reactant 2

HCID 2723910Hydrazine, (2-fluorophenyl)-, hydrochloride (1:1)HCID 23668193Sodium Nitrite

Product 1

HCID 116079241-Azido-2-fluorobenzeneYield 47.4%

Reagents, catalysts & solvents 3

HCID 313Hydrochloric AcidSolventHCID 962WaterSolventHCID 3283Diethyl EtherSolvent2×

Procedure

Sodium nitrite (510 mg) dissolved in 2 ml of water was dropped, under cooling with ice, into a solution of 1.0 g of 2-fluorophenylhydrazine hydrochloride in 5 ml of concentrated hydrochloric acid and 6 ml of diethyl ether. Temperature of the reaction solution was raised to room temperature followed by stirring for 2 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 400 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-599b6c4463fd466e8218bf32d21a6be0
Source dataset
uspto-grants-2010_12
Patent number
US07858800B2

Reaction notes

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