2,5-Difluoroaniline → 2,5-Difluorobenzenediazonium tetrafluoroborate

HRID 1394908Notes

Reaction equation

HRID 1394908 reaction equation
[F:1][B-:2]([F:5])([F:4])[F:3].[N:6]#[O+].[F: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].[F: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 677752,5-DifluoroanilineHCID 11137142Nitrilooxonium tetrafluoroborate

Product 1

HCID 829738342,5-Difluorobenzenediazonium tetrafluoroborate

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 6342AcetonitrileSolvent

Procedure

Nitrosonium tetrafluoroborate (905 mg, 7.75 mmol, 1.00 equiv) was added to a solution of 2,5-difluoroaniline (0.780 mL, 7.75 mmol, 1 equiv) 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 2,5-difluorobenzenediazonium tetrafluoroborate (2-1) as a tan solid. 1H NMR (300 MHz, CD3OD) δ 8.54 (m, 1H), 8.24 (m, 1H), 7.95 (m, 1H).

Workup

  1. filtrationThe precipitate was filtered
  2. customair dried

Sources & evidence

ORD record
ord-c7fc99aa5548474d8b3b086e785e096f
Source dataset
uspto-grants-2008_03
Patent number
US07348440B2

Reaction notes

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