1,2-Dibromobenzene → HCID 101767578, compound

A microsystem composed of three T-shaped micromixers (M1, M2 and M3) and two microtube reactors (R1 and R2) was used. The whole microsystem was dipped in a cooling bath (−78° C.). A solution of o-dibromobenzene (0.27 M) in THF (flow rate: 6 mL/min, 1.62 mmol/min) and a solution of n-BuLi (1.5 M) in n-hexane (flow rate: 1.2 mL/min, 1.8 mmol/min) were introduced to the first T-shaped mixer M1 (inner diameter: 250 μm) by using syringe pumps. The resulting solution was passed through the tube reactor R1 and was mixed with chlorodimethylsilane (HMe2SiCl) (0.65 M) in THF (flow rate: 3 mL/min, 1.95 mmol/min) in the second T-shaped mixer M2 (inner diameter: 500 μm). The solution was introduced to the third T-shaped mixer M3 (inner diameter: 500 μm), where the solution was quenched with methanol (neat, flow rate=3.0 mmol/min). The residence time of the tube reactor R1 (inner diameter: 500 μm, length=50 cm) was 0.82 second. The residence time of the tube reactor R2 (inner diameter: 1,000 μm, length=50 cm) was 2.31 second. After finishing the reaction, an aliquot of the product solution was taken (15 sec) and was analyzed by GC (column, CBP1; 0.25 mm×25 m; initial oven temperature, 50° C.; rate of temperature increase, 10° C./min). As a result, 2-bromophenyldimethylsilane (GC retention time: 14.9 min) was obtained in 68% yield. 1H NMR (400 MHz, CDCl3) δ: 0.40-0.43 (m, 6H), 4.47-4.53 (m, 1H), 7.14-7.27 (m, 2H), 7.42-7.50 (m, 2H); 13C NMR (100 MHz, CDCl3) δ: −3.5, 126.4, 130.6, 130.9, 132.2, 136.4, 139.1. HRMS (EI) m/z: calcd. for C8H11BrSi 213.9813, found 213.9816.

1. customThe whole microsystem was dipped in a cooling bath
2. custom(−78° C.)
3. additionThe solution was introduced to the third T-shaped mixer M3 (inner diameter: 500 μm), where the solution
4. customwas quenched with methanol (neat, flow rate=3.0 mmol/min)
5. waitThe residence time of the tube reactor R2 (inner diameter: 1,000 μm, length=50 cm) was 2.31 second
6. customthe reaction
7. custom(15 sec)
8. customtemperature, 50° C.
9. temperaturerate of temperature increase

ORD record

ord-023657fb097b4a479d49ed7e518f57e6

Source dataset

uspto-grants-2009_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07572927B2