N-bromobutanimide → 209796-22-5

HRID 2267408Notes

Reaction equation

HRID 2267408 reaction equation
[Br:1]N1C(=O)CCC1=O.[S:9]1[CH:13]=[CH:12][C:11]([CH2:14][C:15]#[N:16])=[CH:10]1>C(Cl)(Cl)(Cl)Cl.Cl(O)(=O)(=O)=O.C([O-])(O)=O.[Na+]>[Br:1][C:10]1[S:9][CH:13]=[CH:12][C:11]=1[CH2:14][C:15]#[N:16]

Participants

6

Reactant 2

HCID 67184N-bromobutanimideHCID 837303-Thienylacetonitrile

Product 1

HCID 57428854209796-22-5Yield 43%

Reagents, catalysts & solvents 3

HCID 24247Perchloric AcidCatalystHCID 516892Sodium BicarbonateCatalystHCID 5943Carbon TetrachlorideSolvent

Procedure

Perchloric acid (0.025 mL, 0.28 mmol) was added to a rapidly stirring suspension of N-bromosuccinimide (5.06 g, 28.4 mmol) and 2-(thiophen-3-yl)acetonitrile (3.50 g, 28.4 mmol) in carbon tetrachloride (15 mL). After 4 h at room temperature, the reaction mixture was treated with solid NaHCO3 (100 mg, 1.2 mmol), then filtered and concentrated. The residue was purified by chromatography, eluting with a gradient of 2-15% EtOAc/hexanes to afford pure 2-(2-bromothiophen-3-yl)acetonitrile as a pale green oil (2.44 g, 12.1 mmol, 43% yield). MS (M+H)+ 202/204.

Workup

  1. filtrationfiltered
  2. concentrationconcentrated
  3. customThe residue was purified by chromatography
  4. washeluting with a gradient of 2-15% EtOAc/hexanes

Sources & evidence

ORD record
ord-b8ea3e1c2c3845f99dc9c18a3314e27f
Source dataset
uspto-grants-2010_12
Patent number
US07858785B2

Reaction notes

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