Benzoyl Peroxide → 4-Bromomethyl-2-butoxy-benzoic acid methyl ester

HRID 424802Notes

Reaction equation

[CH3:1][O:2][C:3](=[O:16])[C:4]1[CH:9]=[CH:8][C:7]([CH3:10])=[CH:6][C:5]=1[O:11][CH2:12][CH2:13][CH2:14][CH3:15].C(OOC(=O)C1C=CC=CC=1)(=O)C1C=CC=CC=1.C1C(=O)N([Br:42])C(=O)C1>C(Cl)(Cl)(Cl)Cl>[CH3:1][O:2][C:3](=[O:16])[C:4]1[CH:9]=[CH:8][C:7]([CH2:10][Br:42])=[CH:6][C:5]=1[O:11][CH2:12][CH2:13][CH2:14][CH3:15]

Participants

Conditions

Temperature: 70 °C

Procedure

A mixture of 2-butoxy-4-methyl-benzoic acid methyl ester (0.85 g, 3.8 mmol), dibenzoyl peroxide (100 mg), and NBS (0.68 g, 3.8 mmol) in CCl4 (20 mL) is heated to 70° C. overnight. The solid is filtered off and the filtrate is concentrated to a residue. The residue is purified by flash chromatography to give 4-Bromomethyl-2-butoxy-benzoic acid methyl ester as a syrup (0.6 g, 52%). LC-MS: 301.0 (M+1).

Workup

filtrationThe solid is filtered off
concentrationthe filtrate is concentrated to a residue
customThe residue is purified by flash chromatography

Sources & evidence

ORD record: ord-83a85c2af587485fa568e43b113939b9
Source dataset: uspto-grants-2012_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08106077B2

Reaction notes

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