N-bromobutanimide → 2-Bromomethyl-4-(pyridin-2-yloxy)-benzoic acid ethyl ester

HRID 1480976Notes

Reaction equation

HRID 1480976 reaction equation
[CH2:1]([O:3][C:4](=[O:19])[C:5]1[CH:10]=[CH:9][C:8]([O:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][N:13]=2)=[CH:7][C:6]=1[CH3:18])[CH3:2].C1C(=O)N([Br:27])C(=O)C1>C(Cl)(Cl)(Cl)Cl.C(OOC(C1C=CC=CC=1)=O)(C1C=CC=CC=1)=O>[CH2:1]([O:3][C:4](=[O:19])[C:5]1[CH:10]=[CH:9][C:8]([O:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][N:13]=2)=[CH:7][C:6]=1[CH2:18][Br:27])[CH3:2]

Participants

5

Reactant 2

HCID 67184N-bromobutanimideHCID 898129622-Methyl-4-(pyridin-2-yloxy)-benzoic acid ethyl ester

Product 1

HCID 898128232-Bromomethyl-4-(pyridin-2-yloxy)-benzoic acid ethyl esterYield 123.7%

Reagents, catalysts & solvents 2

HCID 7187Benzoyl PeroxideCatalystHCID 5943Carbon TetrachlorideSolvent

Procedure

A mixture of 2-methyl-4-(pyridin-2-yloxy)-benzoic acid ethyl ester (529 mg), NBS (440 mg), and BzOOBz (25 mg) in CCl4 (10 mL) was refluxed for 6 h; then cooled, solids were filtered off, filtrate was concentrated to give crude product (855 mg). 1H NMR in CDCl3, δ in ppm: 8.2-7.6 (m, 4H), 7.1-6.95 (m, 3H), 4.94 (s, 2H), 4.39 (q, 2H, J=7.0 Hz), 1.41 (t, 3H, J=7.0 Hz).

Workup

  1. temperaturewas refluxed for 6 h
  2. temperaturethen cooled
  3. filtrationsolids were filtered off
  4. concentrationfiltrate was concentrated

Sources & evidence

ORD record
ord-f1062b81ca5d4f808672e29573d4953a
Source dataset
uspto-grants-2016_08
Patent number
US09409892B2

Reaction notes

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