Triethylsilane → 4-Bromo-2-(4-chlorobenzyl)-1-methylbenzene

Temperature

0 °C

(5-Bromo-2-methylphenyl)(4-chlorophenyl)methanone (2, 37.0 g, 121 mmol) and triethylsilane (77.3 mL, 484 mmol) were dissolved in 300 mL of CH3CN and cooled to 0° C. BF3OEt2 (91 mL, 726 mmol) was added and the reaction was heated to 60° C. for 2 hours. GCMS was used to monitor the reaction. Upon completion, the reaction was cooled to 0° C. and quenched with 500 mL saturated aqueous NaHCO3. The aqueous phase was extracted twice with EtOAc. The combined organic layers were washed with H2O and brine, dried over Na2SO4, filtered, and the solvent removed in vacuo. The crude solid was slurried in 20% EtOAc/hexanes and passed over a silica plug to remove residual salts. Concentration of the filtrate provided the title compound as a white solid (22.0 g, 62% yield). 1H NMR (400 MHz, CHLOROFORM-d) δ ppm 7.22 (d, J=2.0 Hz, 1 H), 7.21-7.31 (m, 3 H), 7.04 (d, J=8.3 Hz, 2 H), 7.04 (d, J=8.1 Hz, 2 H), 3.91 (s, 2 H), 2.17 (s, 3 H). GCMS (CH4—Cl) [M+H]+=295.

1. additionBF3OEt2 (91 mL, 726 mmol) was added
2. temperaturethe reaction was heated to 60° C. for 2 hours
3. customthe reaction
4. temperatureUpon completion, the reaction was cooled to 0° C.
5. customquenched with 500 mL saturated aqueous NaHCO3
6. extractionThe aqueous phase was extracted twice with EtOAc
7. washThe combined organic layers were washed with H2O and brine
8. dry with materialdried over Na2SO4
9. filtrationfiltered
10. customthe solvent removed in vacuo
11. customto remove residual salts

ORD record

ord-8169f53302644b32bb822d9314a5b382

Source dataset

uspto-grants-2015_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09200025B2