Bromine → (S)-(+)-5-Bromo-2-(2-methylbutyloxy)benzonitrile

Reaction equation

[CH3:1][C@@H:2]([CH2:13][CH3:14])[CH2:3][O:4][C:5]1[CH:12]=[CH:11][CH:10]=[CH:9][C:6]=1[C:7]#[N:8].[Br:15]Br>>[Br:15][C:10]1[CH:11]=[CH:12][C:5]([O:4][CH2:3][C@@H:2]([CH3:1])[CH2:13][CH3:14])=[C:6]([CH:9]=1)[C:7]#[N:8]

Participants

Reactant 2

HCID 24408Bromine

HCID 53752700(S)-(+)-2-(2-Methylbutyloxy)benzonitrile

Product 1

HCID 53787839(S)-(+)-5-Bromo-2-(2-methylbutyloxy)benzonitrile

Procedure

A mixture of compound 39 (4.25 g, 0.-22 mol), bromine (12.31 g, 0.077 mol was then added and heating continued for another 24 h. The resultant solution was washed with a saturated solution of sodium thiosulphate and finally with water. The dichloromethane solution was dried (MgSO4) and evaporated in vacuo and the crude oil was purified by column chromatography (10% petrol/dichloromethane) to yield a fawn oil.

Workup

additionwas then added
temperatureheating
washThe resultant solution was washed with a saturated solution of sodium thiosulphate and finally with water
dry with materialThe dichloromethane solution was dried (MgSO4)
customevaporated in vacuo
customthe crude oil was purified by column chromatography (10% petrol/dichloromethane)
customto yield a fawn oil

Sources & evidence

ORD record: ord-09d244bbfa50466ca11c62a4415342a0
Source dataset: uspto-grants-2001_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06278028B1

Reaction notes

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