N-bromobutanimide → 4-(Hydroxyimino-bromomethyl)-benzonitrile

HRID 1192787Notes

Reaction equation

HRID 1192787 reaction equation
[Br:1]N1C(=O)CCC1=O.[OH:9][N:10]=[CH:11][C:12]1[CH:19]=[CH:18][C:15]([C:16]#[N:17])=[CH:14][CH:13]=1>C(Cl)Cl>[OH:9][N:10]=[C:11]([Br:1])[C:12]1[CH:19]=[CH:18][C:15]([C:16]#[N:17])=[CH:14][CH:13]=1

Participants

4

Reactant 2

HCID 67184N-bromobutanimideHCID 52147424-Cyanobenzaldehyde oxime

Product 1

HCID 867199294-(Hydroxyimino-bromomethyl)-benzonitrile

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

The compound was prepared according to Tanaka et al. Bull. Chem. Soc. Jpn. 1984, 57, 2184. A 0.05 M solution of N-bromosuccinimide (724 mg, 4.07 mmol, 1.20 eq) in CH2Cl2 was added dropwise to a 0° C. solution of 4-(hydroxyiminomethyl)-benzonitrile (496 mg, 3.39 mmol, 1.00 eq) in CH2Cl2 (50 mL). The solution was warmed to room temperature before being volumetrically partitioned between two different reaction vials. Each vial was then concentrated and the crude residues were used without further purification.

Workup

  1. customThe compound was prepared
  2. custombefore being volumetrically partitioned between two different reaction vials
  3. concentrationEach vial was then concentrated
  4. customthe crude residues were used without further purification

Sources & evidence

ORD record
ord-7c0e216e7f2f4ba09049eb5f7993e94b
Source dataset
uspto-grants-2014_03
Patent number
US08680269B2

Reaction notes

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