Submit a SyntheticPage About SyntheticPages Page Index Browse most recent SyntheticPages View the Leaderboard We value your feedback
  Navigation Buttons

Front Page

Log In

Join Now

Print Version


About this site

Privacy Policy

Copyright Syntheticpages ©2001

Bromination of an electron-rich aromatic ring (3,5-dimethylanisole); 4-bromo-3,5-dimethylanisole

SyntheticPage 156 (2001)
Submitted 31st Aug 2001, published 31st Aug 2001

Mark Birri ([email protected]),
A contribution from the Caddick Group, Sussex

Chemicals Used
3,5-dimethylanisole (Avocado), Bromine (Aldrich), Carbon Tetrachloride (Bulk).

To a solution of 3,5-dimethylanisole (26mL, 183.8mmol) in CCl4 (300mL), cooled to 0oC was added a solution of bromine (9.4mL, 183.8mmol) in CCl4 (150mL) over three hours by the aid of an addition funnel. The reaction mixture was stirred for a further 1/2 h at 0oC. The resulting orange/brown solution was quenched by addition of 3% NaOH solution (500mL). The organic layer was isolated and dried over MgSO4, filtered and concentrated in vacuo to yield a slightly yellow oil (39.5g, 100%).

Author's Comments
The reaction worked well producing only mono-brominated product. Nmr analysis showed the compound to be of sufficiant purity for use without further purification, although it is possible to purify this oil by distillation. Although I myself have only carried out this reaction once, it has been used for the synthesis of the neocarzinostatin naphthoate synthesis numerous times within the group.

1H nmr (300MHz, CDCl3) 2.40 (6H, s), 3.77 (3H, s), 6.66 (2H, s).

Lead Reference
Rucker, M. Brueckner, R. Synlett, 1997, 1187-1189.

Other References

This page has been viewed approximately 282 times since records began.

Get CDX file (Choose "Open this file from its current location" TWICE)

SyntheticPagesTM are for use exclusively by those with training and experience in synthetic chemistry. While contributors are asked to identify hazards and to use methods designed to reduce risk, no formal hazard or risk assessments are included, and these procedures must be conducted at one's own risk. SyntheticPages, its editors, owners and associates do not warrant or guarantee the safety of individuals using these procedures and hereby disclaim any liability for any injuries or damages claimed to have resulted from or related in any way to the procedures herein. Copyright ©2005 Synthetic Pages

Comment on this page!

Registered users may add comments to other pages. If you have already registered, please log in, otherwise you may register here.

Back to Top

By using this site, you agree to its Terms and Conditions