Bromocyclopentane → Methyl 3,5-dichloro-4-(cyclopentyloxy)benzoate

Temperature

80 °C

Methyl 3,5-dichloro-4-hydroxybenzoate (1) (1.00 g, 4.52 mmol) was dissolved in DMF (8 mL) and treated with bromocyclopentane (534 μL, 4.98 mmol), followed by potassium carbonate (937 mg, 6.79 mmol). The mixture was stirred at 80° C. for 3 h and then partitioned between EtOAc (100 mL) and H2O (100 mL). The aqueous phase was extracted with EtOAc (50 mL) and the combined organic phases washed successively with water (5×50 mL) and brine (50 mL), then dried over MgSO4 and filtered. The solvent was removed in vacuo to afford methyl 3,5-dichloro-4-(cyclopentyloxy)benzoate (2) (1.10 g, 84%): 1H NMR (400 MHz, CDCl3) δ: 7.97 (2H, s), 5.04 (1H, m), 3.90 (3H, s), 2.04-1.91 (4H, m), 1.82-1.75 (2H, m), 1.69-1.60 (2H, m).

1. custompartitioned between EtOAc (100 mL) and H2O (100 mL)
2. extractionThe aqueous phase was extracted with EtOAc (50 mL)
3. washthe combined organic phases washed successively with water (5×50 mL) and brine (50 mL)
4. dry with materialdried over MgSO4
5. filtrationfiltered
6. customThe solvent was removed in vacuo

ORD record

ord-1ce85cf82a9243398065a499278f6629

Source dataset

uspto-grants-2016_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09447028B2