4-BROMO-2,6-BIS(1-METHYLETHYL)BENZENAMINE synthesis
- Product Name:4-BROMO-2,6-BIS(1-METHYLETHYL)BENZENAMINE
- CAS Number:80058-84-0
- Molecular formula:C12H18BrN
- Molecular Weight:256.18
24544-04-5
80058-84-0
To a stirred solution of 2,6-diisopropylaniline (14 g, 78.97 mmol, 1.00 eq.) in N,N-dimethylformamide (200 mL) was slowly added dropwise a solution of N-bromosuccinimide (NBS, 14 g, 78.65 mmol, 1.00 eq.) in N,N-dimethylformamide (100 mL) at 0 °C, the dropwise time was controlled to 60 min. The reaction mixture was continued to be stirred at 0 °C for 1 hour. Subsequently, water (900 mL) was added to the reaction system to quench the reaction. The reaction mixture was extracted with ethyl acetate (300 mL). The organic layers were combined and washed sequentially with saturated ammonium chloride solution (3 x 100 mL) and water (1 x 100 mL). The organic layer was dried over anhydrous sodium sulfate and concentrated under reduced pressure to afford 4-bromo-2,6-diisopropylaniline 20.05 g in 99% yield as a red oil.1H NMR (400 MHz, DMSO-d6): δ 6.95 (s, 2H), 4.77 (s, 2H), 5.47-5.39 (m, 1H), 3.04-2.98 (m, 1H) , 1.13 (d, J = 6.8 Hz, 12H) ppm.
24544-04-5
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80058-84-0
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Yield: 100%
Reaction Conditions:
with N-Bromosuccinimide in N,N-dimethyl-formamide at 0 - 5; for 0.333333 h;Inert atmosphere;
Steps:
A solution of NBS (24.59 g, 137 mmol) in DMF (160 mL) was added slowly to a solution of 2,6-diisopropylaniline (25 g, 137 mmol) in DMF (300 mL) at 0-5°C under a nitrogen atmosphere over a period of 20 minutes. The reaction mixture was stirred at 0-5°C. After the reaction was complete, water was added and the oil suspension was stirred at rt. The aqueous layer was decanted out and the remaining oil was dissolved in ethyl acetate. The organic layer was separated, washed water and brine.Evaporation gave light brown oil (35.1 g, 100% yield).
References:
UNIVERSAL DISPLAY CORPORATION;XIA, Chuanjin;YEAGER, Walter;LI, David Zenan;FIORDELISIO, James;MA, Bin;ELSHENAWY, Zeinab;LAYEK, Suman;BARRON, Edward;KOTTAS, Gregg;BROOKS, Jason WO2012/116231, 2012, A2 Location in patent:Page/Page column 120
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80058-84-0
108 suppliers
$24.00/1g