2-Chloro-5-fluoroaniline → HCID 86605053, compound

HRID 1394903Notes

Reaction equation

HRID 1394903 reaction equation
[F:1][B-:2]([F:5])([F:4])[F:3].[N:6]#[O+].[Cl:8][C:9]1[CH:15]=[CH:14][C:13]([F:16])=[CH:12][C:10]=1[NH2:11]>C(#N)C.C(OCC)C>[F:1][B-:2]([F:5])([F:4])[F:3].[Cl:8][C:9]1[CH:15]=[CH:14][C:13]([F:16])=[CH:12][C:10]=1[N+:11]#[N:6]

Participants

5

Reactant 2

HCID 27365092-Chloro-5-fluoroanilineHCID 11137142Nitrilooxonium tetrafluoroborate

Product 1

HCID 86605053HCID 86605053, compound

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 6342AcetonitrileSolvent

Procedure

Nitrosonium tetrafluoroborate (802 mg, 6.87 mmol) was added to a solution of 2-chloro-5-fluoroaniline (1.00 g, 6.87 mmol) in acetonitrile (50 mL) at 0° C. The resulting mixture was stirred for 1 hour, then diluted with ethyl ether (150 mL). The precipitate was filtered and air-dried to give 2-chloro-5-fluorobenzenediazonium tetrafluoroborate (1-1) as an off-white solid. 1H NMR (300 MHz, CD3OD) δ 8.66 (ddd, 1H, J=6.7, 2.1, 1.0 Hz), 8.16 (m, 2H).

Workup

  1. filtrationThe precipitate was filtered
  2. customair-dried

Sources & evidence

ORD record
ord-8532c6da0af74d85845a9c554e88d574
Source dataset
uspto-grants-2008_03
Patent number
US07348440B2

Reaction notes

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