N-bromobutanimide → Methyl 2-(bromomethyl)-4-cyanobenzoate

HRID 2277631Notes

Reaction equation

HRID 2277631 reaction equation
[CH3:1][O:2][C:3](=[O:13])[C:4]1[CH:9]=[CH:8][C:7]([C:10]#[N:11])=[CH:6][C:5]=1[CH3:12].C1C(=O)N([Br:21])C(=O)C1>C(Cl)(Cl)(Cl)Cl.C(OOC(=O)C1C=CC=CC=1)(=O)C1C=CC=CC=1>[CH3:1][O:2][C:3](=[O:13])[C:4]1[CH:9]=[CH:8][C:7]([C:10]#[N:11])=[CH:6][C:5]=1[CH2:12][Br:21]

Participants

5

Reactant 2

HCID 67184N-bromobutanimideHCID 18766060Methyl 4-cyano-2-methylbenzoate

Product 1

HCID 23359115Methyl 2-(bromomethyl)-4-cyanobenzoateYield 100.4%

Reagents, catalysts & solvents 2

HCID 7187Benzoyl PeroxideCatalystHCID 5943Carbon TetrachlorideSolvent

Procedure

A mixture of 4-cyano-2-methyl-benzoic acid methyl ester (12.5 g, 71.35 mmol), NBS (12.7 g, 71.35 mmol) and di-benzoyl peroxide (BPO) (0.8 g, 3.28 mmol) in CCl4 (200 mL) was heated to reflux temperature for 3 hours. After it was cooled to room temperature, the reaction mixture was filtered. The filtrate was concentrated in vacuo to give a crude product (18.2 g) which was used in the next step reaction without further purification.

Workup

  1. temperaturewas heated
  2. temperatureto reflux temperature for 3 hours
  3. filtrationthe reaction mixture was filtered
  4. concentrationThe filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-85972f8c71f340ccadb798db818c093b
Source dataset
uspto-grants-2015_09
Patent number
US09133158B2

Reaction notes

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