Dimethylformamide → 4-(Trimethylsilyl)benzaldehyde

Temperature

-78 °C

Bromo-4-(trimethylsilyl)benzene (1.15 g, 5 mmol) was dissolved in THF (30 ml) and cooled to −78° C. Under argon a 1.6 M solution of n-butyl lithium in hexane (3.13 ml, 5 mmol) was added dropwise keeping the temperature below −70° C. The clear colorless solution was stirred at −78° C. for 15 min and DMF (1.156 ml, 15 mmol) was added quickly. The reaction temperature increased to −68° C. The reaction was stirred for additional 15 min at −78° C., quenched with 1N aqueous hydrogen chloride solution and extracted twice with diethyl ether. The combined organic layers were washed twice with water and once with saturated aqueous sodium chloride solution, dried over sodium sulfate, filtered and the solvent was evaporated to afford the product as a colorless oil (920 mg, 100%). The product was pure enough to be used directly in the next step. MS (ISP) 179.2 (M+H+). 1HNMR (CDCl3, 300 MHz): δ 10.02 (s, 1H) 7.84 (d, 2H), 7.69 (d, 2H), 0.31 (s, 9H).

1. customthe temperature below −70° C
2. temperatureThe reaction temperature increased to −68° C
3. stirringThe reaction was stirred for additional 15 min at −78° C.
4. customquenched with 1N aqueous hydrogen chloride solution
5. extractionextracted twice with diethyl ether
6. washThe combined organic layers were washed twice with water and once with saturated aqueous sodium chloride solution
7. dry with materialdried over sodium sulfate
8. filtrationfiltered
9. customthe solvent was evaporated

ORD record

ord-9a8d06b71af2423ab3e7eed671a905c7

Source dataset

uspto-grants-2010_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07678818B2