N-bromobutanimide → 3-Benzoyloxy-4-chlorobenzyl bromide

HRID 1685652Notes

Reaction equation

HRID 1685652 reaction equation
[C:1]([O:9][C:10]1[CH:11]=[C:12]([CH:15]=[CH:16][C:17]=1F)[CH2:13][Br:14])(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(OC1C=C(C)C=CC=1[Cl:34])(=O)C1C=CC=CC=1.C1C(=O)N(Br)C(=O)C1>C(Cl)(Cl)(Cl)Cl.C(OOC(=O)C1C=CC=CC=1)(=O)C1C=CC=CC=1>[C:1]([O:9][C:10]1[CH:11]=[C:12]([CH:15]=[CH:16][C:17]=1[Cl:34])[CH2:13][Br:14])(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 3

HCID 67184N-bromobutanimideHCID 167478383-Benzoyloxy-4-fluorobenzyl bromideHCID 167492223-Benzoyloxy-4-chlorotoluene

Product 1

HCID 167478403-Benzoyloxy-4-chlorobenzyl bromideYield 62%

Reagents, catalysts & solvents 2

HCID 7187Benzoyl PeroxideCatalystHCID 5943Carbon TetrachlorideSolvent

Procedure

The title compound was prepared by adapting the method for 3-benzoyloxy-4-fluorobenzyl bromide using 3-benzoyloxy-4-chlorotoluene (2.47 g, 10.0 mmol), NBS (1.96 g, 11.0 mmol) and benzoyl peroxide (10 mg) in carbon tetrachloride (25 mL). The residue was purified by flash column chromatography [SiO2, EtOAc/n-hexane (1:40)] to give 3-benzoyloxy-4-chlorobenzyl bromide as a colourless oil (2.012 g, 62%) which solidified on standing and was used without further purification; δH (400 MHz, CDCl3) 4.48 (s, 2H), 7.27 (dd, J=8.2, 2.0, 1H), 7.36 (d, J=2.0, 1H), 7.46 (d, J=8.2, 1H), 7.50-7.58 (m, 2H), 7.64-7.71 (m, 1H), 8.22-8.28 (m, 2H). LRMS (FAB+) m/z (rel. intensity) 325.0 (81, [M+H]+), 327.0 (100, [M+H]+);

Workup

  1. customThe title compound was prepared
  2. customThe residue was purified by flash column chromatography [SiO2, EtOAc/n-hexane (1:40)]

Sources & evidence

ORD record
ord-78b5aac6856f4760a1c64fee63a8c8f6
Source dataset
uspto-grants-2012_04
Patent number
US08148415B2

Reaction notes

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