Water → 4-Amino-3-bromo-2,5-difluorobenzonitrile

HRID 1607179Notes

Reaction equation

HRID 1607179 reaction equation
[Br:1]Br.O.[NH2:4][C:5]1[C:12]([F:13])=[CH:11][C:8]([C:9]#[N:10])=[C:7]([F:14])[CH:6]=1>CC(O)=O>[NH2:4][C:5]1[C:12]([F:13])=[CH:11][C:8]([C:9]#[N:10])=[C:7]([F:14])[C:6]=1[Br:1]

Participants

5

Reactant 3

HCID 962WaterHCID 24408BromineHCID 27359004-Amino-2,5-difluorobenzonitrile

Product 1

HCID 146210194-Amino-3-bromo-2,5-difluorobenzonitrileYield 71%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A mixture of 1.65 mL of Br2, 2 mL of H2O and 5 g of 4-amino-2,5-difluorobenzonitrile in 50 mL of AcOH is stirred at 20°-25° for 16 hours. The solvents are removed in vacuo and the residue partitioned between 100 mL of H2O and 3×200 ml of CH2Cl2. The CH2Cl2 extracts are washed with H2O, saturated NaHCO3, H2O (100 mL each), dried with Na2SO4 and evaporated in vacuo to give 6.89 g of crude 4-amino-3-bromo-2,5-difluorobenzonitrile. This is purified by dry-column chromatography using SiO2 to give 5.38 g (71% yield). Recrystallization from CH2Cl2 /hexane affords analytically pure material, m.p. 106°-108° C.

Workup

  1. customThe solvents are removed in vacuo
  2. customthe residue partitioned between 100 mL of H2O and 3×200 ml of CH2Cl2
  3. washThe CH2Cl2 extracts are washed with H2O, saturated NaHCO3, H2O (100 mL each)
  4. dry with materialdried with Na2SO4
  5. customevaporated in vacuo

Sources & evidence

ORD record
ord-690245e71855466eb051ecc7f75c2a27
Source dataset
uspto-grants-1989_09
Patent number
US04863959

Reaction notes

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