How to convert benzene to 2-nitrostyrene as the major product?
I actually came up with a conversion but I don't know if it's correct or not:
Brominate to form bromobenzene
Nitrate and separate by column chromatography to isolate o-nitrobromobenzene (read)
Vinylate with vinylboroxane/Pd(PPh3)4/K2CO3/DME
Reference: J.Org. Chem. 67 (2002) 4968, Review JCS Chem. Comm. 2009 20-33