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

HRID 463505Notes

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-7acb16505c264cac8d302a8935f8dda1
Source dataset: uspto-grants-1985_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04519946

Reaction notes

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