1-(Neopentyloxy)-4-nitrobenzene synthesis
- Product Name:1-(Neopentyloxy)-4-nitrobenzene
- CAS Number:14225-16-2
- Molecular formula:C11H15NO3
- Molecular Weight:209.24
Yield:14225-16-2 100 %
Reaction Conditions:
Stage #1: 2,2-dimethyl-propanol-1with sodium hydride in N,N-dimethyl-formamide;mineral oil at 0;
Stage #2: 4-Fluoronitrobenzene in N,N-dimethyl-formamide;mineral oil at 25;
Steps:
Step 1. 1-(2,2-Dimethylpropoxy)-4-nitro-benzene
To a solution of 2,2-dimethylpropan-1-ol (3.75 g, 42.5 mmol) in N,N-dimethylformamide (100 mL) was added sodium hydride (2.83 g, 70.8 mmol, 60% in mineral oil) portionwise at 0 °C. The mixture was stirred at 0 °C for 10 min. Then 1-fluoro-4-nitro-benzene (5 g, 35.4 mmol) was added. The mixture was stirred at 25 °C for 3 h. Upon completion, the reaction mixture was quenched by addition water (30 ml) and extracted with ethyl acetate (200 mL x 3). The combined organic layers were washed with brine (50 mL x 3), dried over sodium sulfate, filtered and concentrated in vacuo to give 1-(2,2-dimethylpropoxy)-4-nitro-benzene (5.5 g, 26.6 mmol, 100%) as a yellow oil.1H NMR (400 MHz, DMSO-d6) δ 8.24 - 8.16 (m, 2H), 7.15 (d. J = 9.2 Hz, 2H), 3.79 (s, 2H), 1.01 (s, 9H).
References:
WO2022/266458,2022,A1 Location in patent:Paragraph 0898-0899
(4-nitrophenyl)-, (SP-4-3)- (9CI)](/CAS/20211123/GIF/210693-64-4.gif)
