N-bromobutanimide → Methyl 2-(bromomethyl)-3-nitrobenzoate

HRID 1424504Notes

Reaction equation

HRID 1424504 reaction equation
[CH3:1][C:2]1[C:11]([N+:12]([O-:14])=[O:13])=[CH:10][CH:9]=[CH:8][C:3]=1[C:4]([O:6][CH3:7])=[O:5].[Br:15]N1C(=O)CCC1=O>C(Cl)(Cl)(Cl)Cl.C(OOC(=O)C1C=CC=CC=1)(=O)C1C=CC=CC=1>[Br:15][CH2:1][C:2]1[C:11]([N+:12]([O-:14])=[O:13])=[CH:10][CH:9]=[CH:8][C:3]=1[C:4]([O:6][CH3:7])=[O:5]

Participants

5

Reactant 2

HCID 67184N-bromobutanimideHCID 601165Methyl 2-methyl-3-nitrobenzoate

Product 1

HCID 1487795Methyl 2-(bromomethyl)-3-nitrobenzoateYield 84.9%

Reagents, catalysts & solvents 2

HCID 7187Benzoyl PeroxideCatalystHCID 5943Carbon TetrachlorideSolvent

Procedure

A mixture of methyl 2-methyl-3-nitrobenzoate (1) (18.7 g, 95.8 mmol), N-bromosuccinimide (17.1 g, 96.1 mmol) and benzoyl peroxide (0.7 g, 2.9 mmol) in carbon tetrachloride (500 mL) was refluxed for 20 h. The reaction mixture was cooled and concentrated. Thereafter, it was precipitated and washed by ethyl ether to afford product (2) (22.3 g, 84.8%) as yellowish crystals: mp 68.0-70.0° C. (ref. 67-70° C.).

Workup

  1. temperaturewas refluxed for 20 h
  2. temperatureThe reaction mixture was cooled
  3. concentrationconcentrated
  4. customThereafter, it was precipitated
  5. washwashed by ethyl ether

Sources & evidence

ORD record
ord-dea460f85f4f40ebaef192acb3988d17
Source dataset
uspto-grants-2015_01
Patent number
US08927725B2

Reaction notes

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