Uses
4-Bromo-3-methylphenol may be used in the synthesis of bromo[2-methyl-4-[2-(
t-butyldimethylsilyloxy)ethyloxy]phenyl]bis(triphenylphopshine)nickel(II) (protected alcohol-functionalized initiator) and bromo-[2-methyl-4-[6-(
t-butyldimethylsilyloxy)hexyloxy]phenyl] bis(triphenylphosphine) nickel.
Synthesis
General procedure for the synthesis of 4-bromo-3-methylphenol from m-cresol:
(a) Preparation of 4-bromo-3-methylphenol: 80.0 g (740 mmol) of m-cresol and 400 mL of glacial acetic acid were added to a 2 L three-neck flask under nitrogen protection. The reaction mixture was cooled to 15 °C, 38 mL (742 mmol) of bromine was added slowly dropwise, and the reaction was stirred for 3 h at 15 °C maintaining the temperature. After completion of the reaction, the reaction solution was poured into 1 L of water and extracted with ether. The organic phase was separated and washed with water to neutral pH and subsequently dried with magnesium sulfate. The solvent was removed by evaporation under reduced pressure and the resulting residue was ground in heptane, filtered and dried to give 70 g (50% yield) of a white powdery product with a melting point of 55-56 °C.
References
[1] Letters in Organic Chemistry, 2018, vol. 15, # 8, p. 682 - 687
[2] Bulletin of the Chemical Society of Japan, 1987, vol. 60, # 11, p. 4187 - 4189
[3] Journal of Organic Chemistry, 2005, vol. 70, # 11, p. 4267 - 4271
[4] Synlett, 2011, # 15, p. 2265 - 2269
[5] Journal of Chemical Research - Part S, 2003, # 9, p. 597 - 598
