N-bromobutanimide → Ethyl 2-bromo-(3,5-di-t-butyl-4-hydroxyphenyl)-acetate

HRID 850333Notes

Reaction equation

[C:1]([C:5]1[CH:6]=[C:7]([CH2:16][C:17]([O:19][CH2:20][CH3:21])=[O:18])[CH:8]=[C:9]([C:12]([CH3:15])([CH3:14])[CH3:13])[C:10]=1[OH:11])([CH3:4])([CH3:3])[CH3:2].C1C(=O)N([Br:29])C(=O)C1>C(Cl)(Cl)(Cl)Cl.C(OOC(=O)C1C=CC=CC=1)(=O)C1C=CC=CC=1>[Br:29][CH:16]([C:7]1[CH:8]=[C:9]([C:12]([CH3:13])([CH3:14])[CH3:15])[C:10]([OH:11])=[C:5]([C:1]([CH3:2])([CH3:3])[CH3:4])[CH:6]=1)[C:17]([O:19][CH2:20][CH3:21])=[O:18]

Participants

Conditions

Temperature: 60 °C

Procedure

In carbon tetrachloride (15 mL) was dissolved Intermediate 10 (1.46 g, 5.0 mmol) and NBS (1.33 g, 7.5 mmol). The solution was treated with benzoyl peroxide (~2 mg) and warmed to 60° C. and stirred for 18 hours. The mixture was cooled to room temperature and filtered free of insolubles. The filtrate was evaporated in vacuo to give 2.0 g (>100%) of the crude product as an oil.

Workup

temperatureThe mixture was cooled to room temperature
filtrationfiltered free of insolubles
customThe filtrate was evaporated in vacuo

Sources & evidence

ORD record: ord-ea5fca49619e4c26b2b416391c85a3ea
Source dataset: uspto-grants-2000_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06017918

Reaction notes

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