1-Bromo-3-chlorobenzene → 3-Bromo-5-chlorophenol

A flask containing (1,5-cyclooctadiene)(methoxy)-iridium(I) dimer (84 mg, 0.13 mmol), 4,4′-di-tert butyl-2-2′-dipyridyl (69 mg, 0.26 mmol) and bis(pinacolato)diboron (1.29 g, 5.11 mmol) was purged with Ar, then hexanes (26 mL) and 1-bromo-3-chlorobenzene (1 mL, 8.51 mmol) were added sequentially. The solution was stirred at RT for 18 h. The reaction mixture was concentrated in vacuo, re-dissolved in acetone (26 mL), then oxone (5.23 g, 8.51 mmol) in water (26 mL) added [Caution: exotherm observed]. After 10 min, the reaction mixture was diluted with DCM. The layers separated, and the aqueous layer extracted with DCM. The combined organics were washed with brine, dried and concentrated in vacuo to give the title compound (1.43 g, 81%). LCMS (Method 3): Rt 3.74 min, m/z 205, 207 [M-H+].

1. customwas purged with Ar
2. concentrationThe reaction mixture was concentrated in vacuo
3. dissolutionre-dissolved in acetone (26 mL)
4. waitAfter 10 min
5. customThe layers separated
6. extractionthe aqueous layer extracted with DCM
7. washThe combined organics were washed with brine
8. customdried
9. concentrationconcentrated in vacuo

ORD-Eintrag

ord-54a52132eaea463f878d0ea5404f969d

Quelldatensatz

uspto-grants-2015_11

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US09181242B2