hydroxylamine-O-sulfonic acid → 3-Bromo-6-chloro-2-fluorobenzonitrile

HRID 1363936Notes

Reaction equation

HRID 1363936 reaction equation
[Br:1][C:2]1[C:3]([F:11])=[C:4]([C:7]([Cl:10])=[CH:8][CH:9]=1)[CH:5]=O.[NH2:12]OS(O)(=O)=O>O>[Br:1][C:2]1[C:3]([F:11])=[C:4]([C:7]([Cl:10])=[CH:8][CH:9]=1)[C:5]#[N:12]

Participants

4

Reactant 2

HCID 76284hydroxylamine-O-sulfonic acidHCID 592994573-Bromo-6-chloro-2-fluorobenzaldehyde

Product 1

HCID 509979493-Bromo-6-chloro-2-fluorobenzonitrileYield 100%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
50 °C

Procedure

A suspension of 3-bromo-6-chloro-2-fluorobenzaldehyde (9.0 g, 0.04 mol) and hydroxylamine-O-sulfonic acid (7.50 g, 0.07 mole) in water (300 mL) was heated at 50° C. for eighteen hours. The suspension was cooled and the solid was collected to give 3-bromo-6-chloro-2-fluorobenzonitrile (8.8 g, 0.04 mol): 1H NMR (CDCl3): δ 7.75 (m, 1H), 7.25 (m, 1H).

Workup

  1. temperatureThe suspension was cooled
  2. customthe solid was collected

Sources & evidence

ORD record
ord-d872e9f2fe4b414ab0fdbb220cd19ce3
Source dataset
uspto-grants-2011_02
Patent number
US07888287B2

Reaction notes

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