Water → 4-Bromo-N-methyl-N-(3-methylbutyl)aniline

HRID 543656Notes

Reaction equation

[Br:1]Br.[CH3:3][N:4]([CH2:11][CH2:12][CH:13]([CH3:15])[CH3:14])[C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1.O>C(O)(=O)C>[CH3:3][N:4]([CH2:11][CH2:12][CH:13]([CH3:15])[CH3:14])[C:5]1[CH:6]=[CH:7][C:8]([Br:1])=[CH:9][CH:10]=1

Participants

Conditions

Temperature: 80 °C

Procedure

A solution of 58 g of bromine in 60 ml of acetic acid was added dropwise at about 15° C. over one hour to a mixture of 64 g of the product of Step A in 300 ml of acetic acid and the mixture was stirred at 80° C. for 8 hours and was poured into iced water. The mixture was extracted with methylene chloride and the organic phase was washed with aqueous sodium bicarbonate, with water, dried and evaporated to dryness. The residue was distilled to obtain 70 g of N-methyl-N-(3-methylbutyl)-4-bromo-aniline boiling at 119° C. at 0.5 mm Hg.

Workup

extractionThe mixture was extracted with methylene chloride
washthe organic phase was washed with aqueous sodium bicarbonate, with water
customdried
customevaporated to dryness
distillationThe residue was distilled

Sources & evidence

ORD record: ord-bc2e2a52178745769496f9c045a31cfd
Source dataset: uspto-grants-1984_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04447424

Reaction notes

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