N-bromobutanimide → (4-Amino-3-bromophenyl)acetonitrile

HRID 1711306Notes

Reaction equation

HRID 1711306 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][C:9]#[N:10])=[CH:4][CH:3]=1.C1C(=O)N([Br:18])C(=O)C1>C(#N)C>[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][C:9]#[N:10])=[CH:4][C:3]=1[Br:18]

Participants

4

Reactant 2

HCID 67184N-bromobutanimideHCID 770004-Aminophenylacetonitrile

Product 1

HCID 45037053(4-Amino-3-bromophenyl)acetonitrileYield 92.2%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent2×

Procedure

A solution of 4-aminophenylacetonitrile (1.45 g, 10.9 mmol) in acetonitrile (10 mL) at 0° C. was treated with NBS (1.95 g, 10.9 mmol) in acetonitrile (10 mL) dropwise via an addition funnel. The reaction was allowed to warm to room temperature and then concentrated in vacuo. The crude product was dissolved in EtOAc (50 mL), washed with saturated aqueous NaHCO3 (2×50 mL) and dried (Na2SO4). Removal of the solvent in vacuo afforded the title compound (2.12 g, 92%) as a reddish solid. Mass spectrum (ESI, m/z): Calcd. for C8H7BrN2, 210.9 (M+H), found 211.0.

Workup

  1. concentrationconcentrated in vacuo
  2. dissolutionThe crude product was dissolved in EtOAc (50 mL)
  3. washwashed with saturated aqueous NaHCO3 (2×50 mL)
  4. dry with materialdried (Na2SO4)
  5. customRemoval of the solvent in vacuo

Sources & evidence

ORD record
ord-1a9296351bdb408a8b5e398ccc402edd
Source dataset
uspto-grants-2010_09
Patent number
US07790724B2

Reaction notes

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