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

HRID 708943Notes

Reaction equation

HRID 708943 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 0.05M 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-312b7c46ea924744ba95f60d5869529c
Source dataset
uspto-grants-2015_11
Patent number
US09179681B2

Reaction notes

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