4,4'-di-tert-butyl-2-nitrobiphenyl synthesis

Yield:-

Reaction Conditions:

with nitric acid;acetic anhydride;acetic acid in dichloromethane;

Steps:

Preparation of 4,4'-di-tert-butyl-2-nitro-1,1'-biphenyl

Preparation of 4,4'-di-tert-butyl-2-nitro-1,1'-biphenyl
To 4,4'-di-tert-butylbiphenyl (15.00 g, 56.30 mmol) was added acetic anhydride (300 mL) in a flask that was immersed in a room temperature water bath.
To the suspension was added slowly dropwise a mixture of acetic acid (15 mL, 261.81 mmol) and fuming nitric acid (9.0 mL, 191.43 mmol) over the period of 10 minutes via a pressure equalizer addition funnel.
The solid went into solution and turned yellow.
The mixture was allowed to stir for 30 minutes and checked by GC/MS which showed reaction completion.
The mixture was added to 2.5 L of ice-water and stirred for 1 hour 15 minutes.
The yellow precipitate was collected by vacuum filtration and washed with two 100-mL portions of ice-water.
This crude solid was dissolved in 250 mL of methylene chloride.
The solution was washed with water (250 mL) and 1M aqueous NaOH (250 mL).
The organic phase was dried over anhydrous magnesium sulfate, filtered and concentrated under high vacuum to give the crude as a yellow solid.
The crude solid was dissolved in minimum amount of chloroform for loading in the column cartridge.

References:

US2015/291713,2015,A1