2- Methoxy-5-nitrobenzyl bromide

H.R. Horton, H. Kelly and D.E. Koshland, Environmentally sensitive protein reagents 2-methoxy-5-nitrobenzyl bromide, J. Biol. Chem. 240 (1965) 722-724. 

Me ether [3913-23-3]. 2- Bromomethy[)- J-methoxy-4-nitrobenzene, 9CI. 2-Methoxy-5-nitrobenzyl bromide. 2-Bromomethyl-4-nitroanisole. MNBB. Koshland s reagent II... 

Methoxy-5-nitrobenzyl Bromide (135). This reagent has been used 193) to modify tryptophan residues in a manner similarly to that... 

We first tried to prepare 1-hydroxyyohimbine (23) and its derivatives. With 23 in hand (as described in Section II.D), its methylation with CH2N2 is carried out to provide 1-methoxy derivative 304 (77%) (Scheme 47). Utilizing K2CO3 as a base in DMF, allyl bromide, butyl iodide, and p-nitrobenzyl bromide react successfully with 23, resulting in the formation of 305 (93%), 306 (99%), and 307 (90%), respectively. All of these compounds, including 23 itself, are found to exhibit potent Q 2-blocking activity (2001H1237), and the details will be reported in due course. 

The rate ratio phso/ Meoe for substitution varies from 512 for / -methoxy to 5300 for p-nitrobenzyl bromides (17). The former compound exhibits considerable carbenium ion character in the transition state, hence it reacts faster with MeO (hard-hard interaction). 

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