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

HRID 2277624Notes

Reaction equation

HRID 2277624 reaction equation
[CH3:1][O:2][C:3](=[O:12])[C:4]1[CH:9]=[CH:8][C:7]([F:10])=[CH:6][C:5]=1[CH3:11].C1C(=O)N([Br:20])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:12])[C:4]1[CH:9]=[CH:8][C:7]([F:10])=[CH:6][C:5]=1[CH2:11][Br:20]

Participants

5

Reactant 2

HCID 67184N-bromobutanimideHCID 2782181Methyl 4-fluoro-2-methylbenzoate

Product 1

HCID 18323864Methyl 2-(bromomethyl)-4-fluorobenzoateYield 91.1%

Reagents, catalysts & solvents 2

HCID 7187Benzoyl PeroxideCatalystHCID 5943Carbon TetrachlorideSolvent

Procedure

A mixture of 4-fluoro-2-methyl-benzoic acid methyl ester (12.7 g, 75.5 mmol), NBS (13.4 g, 75.5 mmol), and di-benzoyl peroxide (BPO) (0.85 g, 3.5 mmol) in CCl4 (200 mL) was heated to reflux for 3 hours until all starting material was consumed. After vacuum filtration, the filtrate concentrated in vacuo to give a crude product (17 g, yield 91%), which was used in the next step reaction without further purification.

Workup

  1. temperaturewas heated
  2. temperatureto reflux for 3 hours until all starting material
  3. customwas consumed
  4. filtrationAfter vacuum filtration
  5. concentrationthe filtrate concentrated in vacuo

Sources & evidence

ORD record
ord-0bca1ee61e5049bb82c090464784bca8
Source dataset
uspto-grants-2015_09
Patent number
US09133158B2

Reaction notes

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