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 record

ord-e7b420fca4cd44b99f56ad6c52a98cc7

Source dataset

uspto-grants-2016_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09440974B2