Dimethylformamide → 4-(Trimethylsilyl)benzaldehyde

Temperature

-78 °C

1-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 (1.16 ml, 15 mmol) was added quickly. The reaction temperature raised to −68° C. The reaction was stirred for additional 15 min at −78° C., quenched with 1N aq. HCl solution and extracted twice with diethyl ether. The combined organic layers were washed twice with water and once with sat. aq. NaCl solution, dried over sodium sulfate, filtered and the solvent was evaporated to yield 4-trimethylsilanyl-benzaldehyde (920 mg, 100%) as a colorless oil. 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 raised to −68° C
3. stirringThe reaction was stirred for additional 15 min at −78° C.
4. customquenched with 1N aq. HCl solution
5. extractionextracted twice with diethyl ether
6. washThe combined organic layers were washed twice with water and once with sat. aq. NaCl solution
7. dry with materialdried over sodium sulfate
8. filtrationfiltered
9. customthe solvent was evaporated

ORD record

ord-c337bcd2b9f341288c8cb3ec14e09420

Source dataset

uspto-grants-2009_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07572823B2