Syntheses of 1-Bromo-8-methylnaphthalene and 1-Bromo-5-methylnaphthalene.
The Diels-Alder reaction between 2-methylfuran and 3-bromobenzyne (3), which was generated under mild conditions from 1,3-dibromobenzene and lithium diisopropylamide (LDA), gives a mixture of regioisomeric 1,4-dihydro-1,4-epoxynaphthalenes 4 and 5. A subsequent two-step deoxygenation affords the corresponding 1-bromo-8-methylnaphthalene (1) and 1-bromo-5-methylnaphthalene (2) in high yields.
Department of Chemistry, Dartmouth College, Hanover, New Hampshire 03755-3564, United States.
Evans O
EO
Onyango
Department of Chemistry, Dartmouth College, Hanover, New Hampshire 03755-3564, United States.
Anne R
AR
Kelley
Department of Chemistry, Dartmouth College, Hanover, New Hampshire 03755-3564, United States.
David C
DC
Qian
Department of Chemistry, Dartmouth College, Hanover, New Hampshire 03755-3564, United States.
Gordon W
GW
Gribble