1-Bromo-2-(tert-butyl)benzene Chemical Properties

Boiling point:

96-98 °C(Press: 12 Torr)

Density 

1.236±0.06 g/cm3(Predicted)

storage temp. 

Keep in dark place,Sealed in dry,Room Temperature

Appearance

Colorless to light yellow Liquid

1-Bromo-2-(tert-butyl)benzene Usage And Synthesis

Uses

1-Bromo-2-(tert-butyl)benzene can be used as a key intermediate in the synthesis of various pharmaceuticals.

Synthesis

General procedure for the synthesis of 1-bromo-2-tert-butylbenzene from 2-tert-butylaniline: first, 2-tert-butylaniline (7.46 g, 50 mmol, 15.6 mL) was dissolved in 40% w/w hydrobromic acid (15 mL) and the solution was cooled to less than 5 °C (using an ice/salt bath). A solution of sodium nitrite (7.55 g, 0.11 mol) in 10 mL of water was slowly added at a temperature not exceeding 10 °C, and the addition process lasted for 2 hours. After the diazotization reaction was completed, copper powder (0.20 g) was added. Note: Careful refluxing operation is required due to the violent gas escape during the reaction. After the vigorous nitrogen gas emission subsided, the reaction system was kept at 50 °C for 30 min. Subsequently, the reaction mixture was diluted with 80 mL of water and extracted three times with ether (100 mL each time). The organic layer was washed with 10% KOH solution and dried with Na2SO4. After that, the product was purified by vacuum concentration and silica gel chromatography. Finally, the purified product was distilled at 85 °C (3 mmHg) to obtain 1-bromo-2-tert-butylbenzene (2.88 g, 27% yield). The structure of the product was confirmed by 1H NMR (400 MHz, CDCl3): δ 7.58 (m, 1H, Ph-H), 7.45 (m, 1H, Ph-H), 7.24 (m, 1H, Ph-H), 7.02 (m, 1H, Ph-H), 1.51 (s, 9H, C(CH3)3).

References

[1] Angewandte Chemie - International Edition, 2017, vol. 56, # 40, p. 12288 - 12291
[2] Angew. Chem., 2017, vol. 129, p. 12456 - 12459,4
[3] Patent: WO2015/14835, 2015, A1. Location in patent: Page/Page column 171
[4] Heteroatom Chemistry, 2010, vol. 21, # 5, p. 355 - 360
[5] Supramolecular Chemistry, 2014, vol. 26, # 9, p. 632 - 641

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