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

HRID 389519Notes

Reaction equation

HRID 389519 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>C(O)(=O)C>[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 93.9%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A mixture of bromine (1.65 mL, 32 mmol), water (2 mL), and 4-amino-2,5-difluorobenzonitrile (5 g, 32 mmol) in acetic acid (50 mL) was stirred at RT for 16 h. The mixture was poured into ice cooled saturated sodium bicarbonate solution, causing a solid to separate out. The solid was filtered and washed with water. The solid was then dissolved in DCM, washed with water, dried over sodium sulfate, filtered, and concentrated to afford 7 g (92%) of the title compound. 1H NMR (300 MHz, CDCl3): δ 7.18-7.21 (m, 1H), 4.80 (br. s, 2H).

Workup

  1. additionThe mixture was poured into ice cooled saturated sodium bicarbonate solution
  2. customto separate out
  3. filtrationThe solid was filtered
  4. washwashed with water
  5. dissolutionThe solid was then dissolved in DCM
  6. washwashed with water
  7. dry with materialdried over sodium sulfate
  8. filtrationfiltered
  9. concentrationconcentrated

Sources & evidence

ORD record
ord-462d0895a7ef4bb5b090541c1dc150e0
Source dataset
uspto-grants-2013_02
Patent number
US08378104B2

Reaction notes

Loading…